Cyclohexenonquinolinoyl-derivatives as herbicidal agents

ABSTRACT

Cyclohexenonequinolinoyl derivatives of the formula I                  
 
where:
     R 1  is hydrogen, nitro, halogen, cyano, alkyl, haloalkyl, alkoxyiminomethyl, alkoxy, haloalkoxy, alkylthio, C 1 –C 6 -haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, unsubstituted or substituted amino sulfonyl, unsubstituted or substituted sulfonyl amino, unsubstituted or substituted phenoxy, unsubstituted or substituted heterocyclyloxy, unsubstituted or substituted phenylthio or unsubstituted or substituted heterocyclylthio;   R 2 , R 3  are hydrogen, alkyl, haloalkyl or halogen;   R 4  is substituted (3-oxo-1-cyclohexen-2-yl)carbonyl or substituted (1,3-dioxo-2-cyclohexyl)methylidene;
 
and their agriculturally useful salts;
 
processes for preparing the cyclohexenonequinolinoyl derivatives; compositions comprising them, and the use of these derivatives or compositions comprising them for controlling undesirable plants are described.

The present invention relates to novel cyclohexenonequinolinoyl derivatives of the formula I,

where:

-   R¹ is hydrogen, nitro, halogen, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl,     C₁–C₆-alkoxyiminomethyl, C₁–C₆-alkoxy, C₁–C₆-haloalkoxy,     C₁–C₆-alkylthio, C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl,     C₁–C₆-haloalkylsulfinyl, C₁–C₆-alkylsulfonyl,     C₁–C₆-haloalkylsulfonyl, aminosulfonyl,     N—(C₁–C₆-alkyl)aminosulfonyl, N,N-di-(C₁–C₆-alkyl)aminosulfonyl,     N—(C₁–C₆-alkylsulfonyl)amino, N—(C₁–C₆-haloalkylsulfonyl)amino,     N—(C₁–C₆-alkyl)-N-(C₁–C₆-alkylsulfonyl)amino,     N—(C₁–C₆-alkyl)-N-(C₁–C₆-haloalkylsulfonyl) amino, phenoxy,     heterocyclyloxy, phenylthio or heterocyclylthio, where the four     last-mentioned radicals may be partially or fully halogenated and/or     may carry one to three of the following substituents:     -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or         C₁–C₄-haloalkoxy; -   R², R³ are hydrogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl or halogen; -   R⁴ is a compound IIa or IIb

where

-   R⁵ is halogen, OR⁷, SR⁷, SOR⁸, SO₂R⁸, OSO₂R⁸, POR⁸R⁹, OPR⁸R⁹,     OPOR⁸R⁹, OPSR⁸R⁹, NR¹⁰R¹¹, ONR¹¹R¹², N-linked heterocyclyl or     O—(N-linked heterocyclyl), where the heterocyclyl radical of the two     last-mentioned substituents may be partially or fully halogenated     and/or may carry one to three of the following radicals:     -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or         C₁–C₄-haloalkoxy; -   R⁶ is nitro, halogen, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl,     di-(C₁–C₆-alkoxy)methyl, di-(C₁–C₆-alkylthio)methyl,     (C₁–C₆-alkoxy)(C₁–C₆-alkylthio)methyl, hydroxy, C₁–C₆-alkoxy,     C₁–C₆-haloalkoxy, C₁–C₆-alkoxycarbonyloxy, C₁–C₆-alkylthio,     C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl,     C₁–C₆-alkylsulfonyl, C₁–C₆-haloalkylsulfonyl, C₁–C₆-alkylcarbonyl,     C₁–C₆-haloalkylcarbonyl, C₁–C₆-alkoxycarbonyl or     C₁–C₆-haloalkoxycarbonyl; -   or -   two radicals R⁶, which are linked to the same carbon, together form     an —O—(CH₂)_(m), —O—(CH₂)_(m)—S—, —S—(CH₂)_(m)—S—, —O—(CH₂)_(n)— or     —S—(CH₂)_(n) chain which may be substituted by one to three radicals     from the following group:     -   halogen, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl or         C₁–C₄-alkoxycarbonyl;     -   or -   two radicals R⁶, which are linked to the same carbon, together form     a —(CH₂)_(p) chain which may be interrupted by oxygen or sulfur     and/or may be substituted by one to four radicals from the following     group:     -   halogen, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl or         C₁–C₄-alkoxycarbonyl; -   or -   two radicals R⁶, which are linked to the same carbon, together form     a methylidene group which may be substituted by one or two radicals     from the following group:     -   halogen, hydroxyl, formyl, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl,         C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio,         C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl,         C₁–C₆-haloalkylsulfinyl, C₁–C₆-alkylsulfonyl or         C₁–C₆-haloalkylsulfonyl; -   or -   two radicals R⁶, which are linked to the same carbon, together with     this carbon form a carbonyl group; -   or -   two radicals R⁶, which are linked to different carbons, together     form a —(CH₂)_(n) chain which may be substituted by one to three     radicals from the following group:     -   halogen, C₁–C₆-alkyl, C₁–C₆-alkoxy, hydroxyl or         C₁–C₆-alkoxycarbonyl; -   R⁷ is C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-haloalkenyl, C₃–C₆-alkynyl,     C₃–C₆-haloalkynyl, C₃–C₆-cycloalkyl, C₁–C₂₀-alkylcarbonyl,     C₂–C₆-alkenylcarbonyl, C₂–C₆-alkynylcarbonyl,     C₃–C₆-Cycloalkylcarbonyl, C₁–C₆-alkoxycarbonyl,     C₃–C₆-alkenyloxycarbonyl, C₃–C₆-alkynyloxycarbonyl,     (C₁–C₂₀-alkylthio)carbonyl, C₁–C₆-alkylaminocarbonyl,     C₃–C₆-alkenylaminocarbonyl, C₃–C₆-alkynylaminocarbonyl, N,     N-di-(C₁–C₆-alkyl) aminocarbonyl, N—(C₃–C₆-alkenyl)-N-(C₁–C₆-alkyl)     aminocarbonyl, N—(C₃–C₆-alkynyl)-N-(C₁–C₆-alkyl)aminocarbonyl,     N—(C₁–C₆-alkoxy)-N-(C₁–C₆-alkyl) aminocarbonyl, N—(C₃–C₆-alkenyl)     —N—(C₁–C₆-alkoxy) aminocarbonyl,     N—(C₃–C₆-alkynyl)-N-(C₁–C₆-alkoxy)aminocarbonyl,     di-(C₁–C₆-alkyl)-aminothiocarbonyl, C₁–C₆-alkylcarbonyl-C₁–C₆-alkyl,     C₁–C₆-alkoxyimino-C₁–C₆-alkyl, N—(C₁–C₆-alkylamino)imino-C₁–C₆-alkyl     or N,N-di-(C₁–C₆-alkylamino)imino-C₁–C₆-alkyl, where the     abovementioned alkyl, cycloalkyl and alkoxy radicals may be     partially or fully halogenated and/or may carry one to three of the     following groups:     -   cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio, di-(C₁–C₄alkyl)amino,         C₁–C₄-alkylcarbonyl, C₁–C₄-alkoxycarbonyl,         C₁–C₄-alkoxy-C₁–C₄-alkoxycarbonyl, di-(C₁–C₄-alkyl)         amino-C₁–C₄-alkoxycarbonyl, hydroxycarbonyl,         C₁–C₄-alkylaminocarbonyl, di-(C₁–C₄-alkyl)aminocarbonyl,         aminocarbonyl, C₁–C₄-alkylcarbonyloxy or C₃–C₆-cycloalkyl;     -   phenyl, heterocyclyl, phenyl-C₁–C₆-alkyl,         heterocyclyl-C₁–C₆-alkyl, phenylcarbonyl-C₁–C₆-alkyl,         heterocyclylcarbonyl-C₁–C₆-alkyl, phenylcarbonyl,         heterocyclylcarbonyl, phenoxycarbonyl, heterocyclyloxycarbonyl,         phenoxythiocarbonyl, heterocyclyloxythiocarbonyl,         phenoxy-C₁–C₆-alkylcarbonyl,         heterocyclyloxy-C₁–C₆-alkylcarbonyl, phenylaminocarbonyl,         N—(C₁–C₆-alkyl)-N-(phenyl)aminocarbonyl,         heterocyclylaminocarbonyl, N—(C₁–C₆-alkyl)-N-(heterocyclyl)         aminocarbonyl, phenyl-C₂–C₆-alkenylcarbonyl or         heterocyclyl-C₂–C₆-alkenylcarbonyl, where the phenyl and the         heterocyclyl radical of the 20 last-mentioned substituents may         be partially or fully halogenated and/or may carry one to three         of the following radicals:     -   nitro, cyano, C₁–C₄ alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or         C₁–C₄-haloalkoxy; -   R⁸, R⁹ are C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-haloalkenyl,     C₃–C₆-alkynyl, C₃–C₆-haloalkynyl, C₃–C₆-Cycloalkyl, hydroxyl,     C₁–C₆-alkoxy, amino, C₁–C₆-alkylamino, C₁–C₆-haloalkylamino,     di-(C₁–C₆alkyl)amino or di-(C₁–C₆-haloalkyl)amino, where the     abovementioned alkyl, cycloalkyl and alkoxy radicals may be     partially or fully halogenated and/or may carry one to three of the     following groups:     -   cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio, di-(C₁–C₄alkyl)amino,         C₁–C₄-alkylcarbonyl, C₁–C₄-alkoxycarbonyl,         C₁–C₄-alkoxy-C₁–C₄-alkoxycarbonyl,         di-(C₁–C₄-alkyl)amino-C₁–C₄-alkoxycarbonyl, hydroxycarbonyl,         C₁–C₄-alkylaminocarbonyl, di-(C₁–C₄-alkyl)aminocarbonyl,         aminocarbonyl, C₁–C₄-alkylcarbonyloxy or C₃–C₆-cycloalkyl;     -   phenyl, heterocyclyl, phenyl-C₁–C₆-alkyl,         heterocyclyl-C₁–C₆-alkyl, phenoxy, heterocyclyloxy, where the         phenyl and the heterocyclyl radical of the last-mentioned         substituents may be partially or fully halogenated and/or may         carry one to three of the following radicals:     -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or         C₁–C₄-haloalkoxy; -   R¹⁰ is C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-haloalkenyl, C₃–C₆-alkynyl,     C₃–C₆-haloalkynyl, C₃–C₆-cycloalkyl, hydroxyl, C₁–C₆-alkoxy,     C₃–C₆-alkenyloxy, C₃–C₆-alkynyloxy, amino, C₁–C₆-alkylamino,     di-(C₁–C₆-alkyl)amino or C₁–C₆-alkylcarbonylamino, where the     abovementioned alkyl, cycloalkyl and alkoxy radicals may be     partially or fully halogenated and/or may carry one to three     radicals from the following group:     -   cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio, di-(C₁–C₄-alkyl)amino,         C₁–C₄-alkylcarbonyl, C₁–C₄-alkoxycarbonyl,         C₁–C₄-alkoxy-C₁–C₄-alkoxycarbonyl,         di-(C₁–C₄-alkyl)amino-C₁–C₄-alkoxycarbonyl, hydroxycarbonyl,         C₁–C₄-alkylaminocarbonyl, di-(C₁–C₄-alkyl)aminocarbonyl,         aminocarbonyl, C₁–C₄-alkylcarbonyloxy or C₃–C₆-cycloalkyl;         phenyl, heterocyclyl, phenyl-C₁–C₆-alkyl or         heterocyclyl-C₁–C₆-alkyl, where the phenyl or heterocyclyl         radical of the four last-mentioned substituents may be partially         or fully halogenated and/or may carry one to three of the         following radicals:     -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or         C₁–C₄-haloalkoxy; -   R¹¹, R¹² are C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-alkynyl or     C₁–C₆-alkylcarbonyl; -   l is 0 to 6; -   m is 2 to 4; -   n is 1 to 5; -   p is 2 to 5;     and their agriculturally useful salts.

Moreover, the invention relates to processes for preparing compounds of the formula I, to compositions comprising them and to the use of these derivatives or the compositions comprising them for controlling harmful plants.

The literature, for example WO 98/12 180 and EP-A 283 261, discloses quinolinoyl or fused phenyl derivatives which are linked to an unsubstituted or substituted (1-hydroxy-3-oxo-cyclohex-1-en-2-yl)carbonyl radical. However, the herbicidal properties of the prior art compounds and their compatibility with crop plants are not entirely satisfactory.

It is an object of the present invention to provide other biologically, in particular herbicidally, active compounds.

We have found that this object is achieved by the cyclohexenonequinolinoyl derivatives of the formula I and their herbicidal action.

Furthermore, we have found herbicidal compositions which comprise the compounds I and have very good herbicidal action. Moreover, we have found processes for pr paring these compositions and methods for controlling undesirable vegetation using the compounds I.

Depending on the substitution pattern, the compounds of the formula I may contain one or more chiral centers, in which case they are present as enantiomers or mixtures of diastereomers. The invention provides both the pure enantiomers or diastereomers and their mixtures.

The compounds of the formula I may also be present in the form of their agriculturally useful salts, where the type of salt is usually immaterial. In general, the salts of those cations and the acid addition salts of those acids are suitable whose cations and anions, respectively, do not negatively affect the herbicidal action of the compounds I.

Suitable cations are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium, where, if desired, one to four hydrogen atoms may be replaced by C₁–C₄-alkyl, hydroxy-C₁–C₄-alkyl, C₁–C₄-alkoxy-C₁–C₄-alkyl, hydroxy-C₁–C₄-alkoxy-C₁–C₄-alkyl, phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C₁–C₄-alkyl)sulfonium and sulfoxonium ions, preferably tri(C₁–C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of C₁–C₄-alkanoic acids, preferably formate, acetate, propionate and butyrate.

The organic moieties mentioned for the substituents R¹–R¹² or as radicals on phenyl and heterocyclyl radicals are collective terms for individual enumerations of the particular group members. All hydrocarbon chains, i.e. all alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfynyl, haloalkylsulfynyl, alkylsulfonyl, haloalkylsulfonyl, N-alkylaminosulfonyl, N,N-dialkylaminosulfonyl, N-alkylamino, N,N-dialkylamino, N-haloalkylamino, N-alkoxyamino, N-alkoxy-N-alkylamino, N-alkylcarbonylamino, N-alkylsulfonylamino, N-haloalkylsulfonylamino, N-alkyl-N-alkylsulfonylamino, N-alkyl-N-haloalkylsulfonylamino, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, alkylthiocarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, alkoxyalkyl, dialkoxymethyl, dialkylthiomethyl, (alkoxy)(alkylthio)methyl, alkylcarbonylalkyl, alkoxyiminomethyl, alkoxyiminoalkyl, N-(alkylamino)iminoalkyl, N-(dialkylamino)iminoalkyl, phenylalkenylcarbonyl, heterocyclylalkenylcarbonyl, phenoxyalkylcarbonyl, heterocyclyloxyalkylcarbonyl, N-alkoxy-N-alkylaminocarbonyl, N-alkyl-N-phenylaminocarbonyl, N-alkyl-N-heterocyclylaminocarbonyl, alkoxycarbonyloxy, phenylalkyl, heterocyclylalkyl, phenylcarbonylalkyl, heterocyclylcarbonylalkyl, dialkylaminoalkoxycarbonyl, alkoxyalkoxycarbonyl, alkenylcarbonyl, alkenyloxycarbonyl, alkenylaminocarbonyl, N-alkenyl-N-alkylaminocarbonyl, N-alkenyl-N-alkoxyaminocarbonyl, alkynylcarbonyl, alkynyloxycarbonyl, alkynylaminocarbonyl, N-alkynyl-N-alkylaminocarbonyl, N-alkynyl-N-alkoxyaminocarbonyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkenyloxy, alkynyloxy and alkoxyalkoxy moieties, may be straight-chain or branched. Unless indicated otherwise, halogenated substituents preferably carry one to five identical or different halogen atoms. The term “halogen” in each case represents fluorine, chlorine, bromine or iodine.

Examples of other meanings are:

-   -   C₁–C₄-alkyl: for example methyl, ethyl, propyl, 1-methylethyl,         butyl, 1-methylpropyl, 2-methylpropyl or 1,1-dimethylethyl;     -   C₁–C₆-alkyl, and the alkyl moieties of         C₁–C₆-alkoxyimino-C₁–C₆-alkyl,         N—(C₁–C₆-alkylamino)imino-C₁–C₆-alkyl,         N-(di-C₁–C₆-alkylamino)imino-C₁–C₆-alkyl,         N—(C₁–C₆-alkoxy)-N-(C₁–C₆-alkyl)-aminocarbonyl,         N—(C₃–C₆-alkenyl)-N-(C₁–C₆-alkyl)aminocarbonyl,         (C₃–C₆-alkynyl)-N-(C₁–C₆-alkyl)aminocarbonyl,         N—(C₁–C₆-alkyl)-N-phenylaminocarbonyl,         N—(C₁–C₆-alkyl)-N-heterocyclylaminocarbonyl, phenyl-1–C₆-alkyl,         N—(C₁–C₆-alkyl)-N-(C₁–C₆-alkylsulfonyl)amino,         N—(C₁–C₆-alkyl)-N(C₁–C₆-haloalkylsulfonyl)amino,         heterocyclyl-C₁–C₆-alkyl, phenylcarbonyl-C₁–C₆-alkyl,         heterocyclylcarbonyl-C₁–C₆-alkyl: C₁–C₄-alkyl as mentioned         above, and also, for example, pentyl, 1-methylbutyl,         2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl,         hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl,         2-methylpentyl, 3-methylpentyl, 4-methylpentyl,         1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,         2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl,         1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,         1-ethyl-1-methylpropyl or 1-ethyl-3-methylpropyl;     -   C₁–C₄-haloalkyl: a C₁–C₄-alkyl radical as mentioned above which         is partially or fully substituted by fluorine, chlorine, bromine         and/or iodine, i.e., for example, chloromethyl, dichloromethyl,         trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,         chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,         2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl,         2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,         2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,         2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl,         3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl,         2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl,         2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl,         3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl,         heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl,         1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl,         4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl;     -   C₁–C₆-haloalkyl, and the haloalkyl moieties of         N—C₁–C₆-haloalkylamino: C₁–C₄-haloalkyl, as mentioned above, and         also, for example, 5-fluoropentyl, 5-chloropentyl,         5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl,         6-chlorohexyl, 6-bromohexyl, 6-iodohexyl or dodecafluorohexyl;     -   C₁–C₄-alkoxy: for example methoxy, ethoxy, propoxy,         1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or         1,1-dimethylethoxy;     -   C₁–C₆-alkoxy, and the alkoxy moieties of N—C₁–C₆-alkoxyamino,         di-(C₁–C₆-alkoxy)methyl, (C₁–C₆-alkoxy)(C₁–C₆-alkylthio)-methyl,         C₁–C₆-alkoxyiminomethyl, C₁–C₆-alkoxyimino-C₁–C₆-alkyl,         N—(C₁–C₆-alkoxy)-N-(C₁–C₆-alkyl) aminocarbonyl,         N—(C₃–C₆-alkenyl)-N-(C₁–C₆-alkoxy)aminocarbonyl and         N—(C₃–C₆-alkynyl)-N-(C₁–C₆-alkoxy)aminocarbonyl: C₁–C₄-alkoxy as         mentioned above, and also, for example, pentoxy, 1-methylbutoxy,         2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy,         1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy,         hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy,         4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy,         1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy,         3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy,         1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy,         1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy;     -   C₁–C₄-haloalkoxy: a C₁–C₄-alkoxy radical as mentioned above         which is partially or fully substituted by fluorine, chlorine,         bromine and/or iodine, i.e., for example, fluoromethoxy,         difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy,         bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy,         2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy,         2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,         2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,         2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy,         3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy,         2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy,         2,3-difluoropropoxy, 2,3-dichloropropoxy,         3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy,         2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy,         1-(fluoromethyl)-2-fluoroethoxy,         1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy,         4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or         nonafluorobutoxy;     -   C₁–C₆-haloalkoxy: C₁–C₄-haloalkoxy as mentioned above, and also,         for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy,         5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy,         6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or         dodecafluorohexoxy;     -   C₁–C₄-alkylthio: for example methylthio, ethylthio, propylthio,         1-methylethylthio, butylthio, 1-methylpropylthio,         2-methylpropylthio or 1,1-dimethylethylthio;     -   C₁–C₆-alkylthio, and the alkylthio moieties of         (C₁–C₆-alkylthio)carbonyl, di-(C₁–C₆-alkylthio)methyl and         (C₁–C₆-alkoxy)-(C₁–C₆-alkylthio)methyl: C₁–C₄-alkylthio as         mentioned above, and also, for example, pentylthio,         1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio,         2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio,         1,1-dimethylpropylthio, 1,2-dimethylpropylthio,         1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio,         4-methylpentylthio, 1,1-dimethylbutylthio,         1,2-dimethylbutylthio, 1,3-dimethylbutylthio,         2,2-dimethylbutylthio, 2,3-dimethylbutylthio,         3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio,         1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio,         1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio;     -   C₁–C₂₀-alkylthio as alkylthio radical of         (C₁–C₂₀-alkylthio)carbonyl: C₁–C₆-alkylthio as mentioned above,         and also, for example, heptylthio, octylthio, hexadecylthio or         octadecylthio;     -   C₁–C₄-haloalkylthio: a C₁–C₄-alkylthio radical as mentioned         above which is partially or fully substituted by fluorine,         chlorine, bromine and/or iodine, i.e., for example,         fluoromethylthio, difluoromethylthio, trifluoromethylthio,         chlorodifluoromethylthio, bromodifluoromethylthio,         2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio,         2-iodoethylthio, 2,2-difluoroethylthio,         2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio,         2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio,         2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio,         2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio,         3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio,         2,2-difluoropropylthio, 2,3-difluoropropylthio,         2,3-dichloropropylthio, 3,3,3-trifluoropropylthio,         3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio,         heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio,         1-(chloromethyl)-2-chloroethylthio,         1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio,         4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio;     -   C₁–C₆-haloalkylthio: C₁–C₄-haloalkylthio, as mentioned above,         and also, for example, 5-fluoropentylthio, 5-chloropentylthio,         5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio,         6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio,         6-iodohexylthio or dodecafluorohexylthio;     -   C₁–C₆-alkylsulfinyl (C₁–C₆-alkyl-S(═O)—): for example         methylsulfinyl, ethylsulfinyl, propylsulfinyl,         1-methylethylsulfinyl, butylsulfinyl, l-methylpropylsulfinyl,         2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl,         pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl,         3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl,         1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl,         1,2-dimethylpropylsulfinyl, hexylsulfinyl,         1-methylpentylsulfinyl, 2-methylpentylsulfinyl,         3-methylpentylsulfinyl, 4-methylpentylsulfinyl,         1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl,         1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl,         2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl,         1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl,         1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl,         1-ethyl-1-methylpropylsulfinyl or         1-ethyl-2-methylpropylsulfinyl;     -   C₁–C₆-haloalkylsulfinyl: a C₁–C₆-alkylsulfinyl radical as         mentioned above which is partially or fully substituted by         fluorine, chlorine, bromine and/or iodine, i.e., for example,         fluoromethylsulfinyl, difluoromethylsulfinyl,         trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl,         bromodifluoromethylsulfinyl, 2-fluoroethylsulfinyl,         2-chloroethylsulfinyl, 2-bromoethylsulfinyl,         2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl,         2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl,         2-chloro-2-fluoroethylsulfinyl,         2-chloro-2,2-difluoroethylsulfinyl,         2,2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl,         2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl,         2-chloropropylsulfinyl, 3-chloropropylsulfinyl,         2-bromopropylsulfinyl, 3-bromopropylsulfinyl,         2,2-difluoropropylsulfinyl, 2,3-difluoropropylsulfinyl,         2,3-dichloropropylsulfinyl, 3,3,3-trifluoropropylsulfinyl,         3,3,3-trichloropropylsulfinyl,         2,2,3,3,3-pentafluoropropylsulfinyl, heptafluoropropylsulfinyl,         1-(fluoromethyl)-2-fluoroethylsulfinyl,         1-(chloromethyl)-2-chloroethylsulfinyl,         1-(bromomethyl)-2-bromoethylsulfinyl, 4-fluorobutylsulfinyl,         4-chlorobutylsulfinyl, 4-bromobutylsulfinyl,         nonafluorobutylsulfinyl, 5-fluoropentylsulfinyl,         5-chloropentylsulfinyl, 5-bromopentylsulfinyl,         5-iodopentylsulfinyl, undecafluoropentylsulfinyl,         6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl,         6-bromohexylsulfinyl, 6-iodohexylsulfinyl or         dodecafluorohexylsulfinyl;     -   C₁–C₆-alkylsulfonyl (C₁–C₆-alkyl-S(═O)₂—), and the alkylsulfonyl         radicals of N—(C₁–C₆-alkylsulfonyl)amino and         N—(C₁–C₆-alkyl)-N-(C₁–C₆-alkylsulfonyl)amino: for example,         methylsulfonyl, ethylsulfonyl, propylsulfonyl,         1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl,         2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl,         pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl,         3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl,         1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl,         1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl,         2-methylpentylsulfonyl, 3-methylpentylsulfonyl,         4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl,         1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl,         2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl,         3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl,         2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl,         1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or         1-ethyl-2-methylpropylsulfonyl;     -   C₁–C₆-haloalkylsulfonyl, and the haloalkylsulfonyl radicals of         N—(C₁–C₆-haloalkylsulfonyl)amino and         N—(C₁–C₆-alkyl)-N-(C₁–C₆-haloalkylsulfonyl)amino: a         C₁–C₆-alkylsulfonyl radical as mentioned above which is         partially or fully substituted by fluorine, chlorine, bromine         and/or iodine, i.e., for example, fluoromethylsulfonyl,         difluoromethylsulfonyl, trifluoromethylsulfonyl,         chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl,         2-fluoroethylsulfonyl, 2-chloroethylsulfonyl,         2-bromoethylsulfonyl, 2-iodoethylsulfonyl,         2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl,         2-chloro-2-fluoroethylsulfonyl,         2-chloro-2,2-difluoroethylsulfonyl,         2,2-dichloro-2-fluoroethylsulfonyl,         2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl,         2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl,         2-chloropropylsulfonyl, 3-chloropropylsulfonyl,         2-bromopropylsulfonyl, 3-bromopropylsulfonyl,         2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl,         2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl,         3,3,3-trichloropropylsulfonyl,         2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl,         1-(fluoromethyl)-2-fluoroethylsulfonyl,         1-(chloromethyl)-2-chloroethylsulfonyl,         1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl,         4-chlorobutylsulfonyl, 4-bromobutylsulfonyl,         nonafluorobutylsulfonyl, 5-fluoropentylsulfonyl,         5-chloropentylsulfonyl, 5-bromopentylsulfonyl,         5-iodopentylsulfonyl, 6-fluorohexylsulfonyl,         6-bromohexylsulfonyl, 6-iodohexylsulfonyl or         dodecafluorohexylsulfonyl;     -   C₁–C₆-alkylamino, and the alkylamino radicals of         N—(C₁–C₆-alkylamino)imino-C₁–C₆-alkyl: for example methylamino,         ethylamino, propylamino, 1-methylethylamino, butylamino,         1-methylpropylamino, 2-methylpropylamino,         1,1-dimethylethylamino, pentylamino, 1-methylbutylamino,         2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino,         1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino,         1,2-dimethylpropylamino, 1-methylpentylamino,         2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino,         1,1-dimethylbutylamino, 1,2-dimethylbutylamino,         1,3-dimethylbutylamino, 2,2-dimethylbutylamino,         2,3-dimethylbutylamino, 3,3-dimethylbutylamino,         1-ethylbutylamino, 2-ethylbutylamino,         1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino,         1-ethyl-1-methylpropylamino or 1-ethyl-2-methylpropylamino;     -   (C₁–C₄-alkylamino)sulfonyl: for example methylaminosulfonyl,         ethylaminosulfonyl, propylaminosulfonyl,         1-methylethylaminosulfonyl, butylaminosulfonyl,         1-methylpropylaminosulfonyl, 2-methylpropylaminosulfonyl or         1,1-dimethylethylaminosulfonyl;     -   (C₁–C₆-alkylamino)sulfonyl: (C₁–C₄-alkylamino)sulfonyl, as         mentioned above, and also, for example, pentylaminosulfonyl,         1-methylbutylaminosulfonyl, 2-methylbutylaminosulfonyl,         3-methylbutylaminosulfonyl, 2,2-dimethylpropylaminosulfonyl,         1-ethylpropylaminosulfonyl, hexylaminosulfonyl,         1,1-dimethylpropylaminosulfonyl,         1,2-dimethylpropylaminosulfonyl, 1-methylpentylaminosulfonyl,         2-methylpentylaminosulfonyl, 3-methylpentylaminosulfonyl,         4-methylpentylaminosulfonyl, 1,1-dimethylbutylaminosulfonyl,         1,2-dimethylbutylaminosulfonyl, 1,3-dimethylbutylaminosulfonyl,         2,2-dimethylbutylaminosulfonyl, 2,3-dimethylbutylaminosulfonyl,         3,3-dimethylbutylaminosulfonyl, 1-ethylbutylaminosulfonyl,         2-ethylbutylaminosulfonyl, 1,1,2-trimethylpropylaminosulfonyl,         1,2,2-trimethylpropylaminosulfonyl,         1-ethyl-1-methylpropylaminosulfonyl or         1-ethyl-2-methylpropylaminosulfonyl;     -   di-(C₁–C₄-alkyl)aminosulfonyl: for example         N,N-dimethylaminosulfonyl, N,N-diethylaminosulfonyl,         N,N-di-(1-methylethyl)aminosulfonyl, N,N-dipropylaminosulfonyl,         N,N-dibutylaminosulfonyl, N,N-di-(1-methylpropyl)aminosulfonyl,         N,N-di-(2-methylpropyl)aminosulfonyl,         N,N-di-(1,1-dimethylethyl)aminosulfonyl,         N-ethyl-N-methylaminosulfonyl, N-methyl-N-propylaminosulfonyl,         N-methyl-N-(1-methylethyl)aminosulfonyl,         N-butyl-N-methylaminosulfonyl,         N-methyl-N-(1-methylpropyl)aminosulfonyl,         N-methyl-N-(2-methylpropyl)aminosulfonyl,         N-(1,1-dimethylethyl)-N-methylaminosulfonyl,         N-ethyl-N-propylaminosulfonyl,         N-ethyl-N-(1-methylethyl)aminosulfonyl,         N-butyl-N-ethylaminosulfonyl,         N-ethyl-N-(1-methylpropyl)aminosulfonyl,         N-ethyl-N-(2-methylpropyl)aminosulfonyl,         N-ethyl-N-(1,1-dimethylethyl)aminosulfonyl,         N-(1-methylethyl)-N-propylaminosulfonyl, N-butyl-N-propyl         aminosulfonyl, N-(1-methylpropyl)-N-propylaminosulfonyl,         N-(2-methylpropyl)-N-propylaminosulfonyl,         N-(1,1-dimethylethyl)-N-propylaminosulfonyl,         N-butyl-N-(1-methylethyl)aminosulfonyl,         N-(1-methylethyl)-N-(1-methylpropyl)aminosulfonyl,         N-(1-methylethyl)-N-(2-methylpropyl)aminosulfonyl,         N-(1,1-dimethylethyl)-N-(1-methylethyl)aminosulfonyl,         N-butyl-N-(1-methylpropyl)aminosulfonyl,         N-butyl-N-(2-methylpropyl)aminosulfonyl,         N-butyl-N-(1,1-dimethylethyl)aminosulfonyl,         N-(1-methylpropyl)-N-(2-methylpropyl)aminosulfonyl,         N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminosulfonyl or         N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminosulfonyl;     -   di-(C₁–C₆-alkyl)aminosulfonyl: di-(C₁–C₄-alkyl)aminosulfonyl, as         mentioned above, and also, for example,         N-methyl-N-pentylaminosulfonyl,         N-methyl-N-(1-methylbutyl)aminosulfonyl,         N-methyl-N-(2-methylbutyl)aminosulfonyl,         N-methyl-N-(3-methylbutyl)aminosulfonyl,         N-methyl-N-(2,2-dimethylpropyl)aminosulfonyl,         N-methyl-N-(1-ethylpropyl)aminosulfonyl,         N-methyl-N-hexylaminosulfonyl,         N-methyl-N-(1,1-dimethylpropyl)aminosulfonyl,         N-methyl-N-(1,2-dimethylpropyl)aminosulfonyl,         N-methyl-N-(1-methylpentyl)aminosulfonyl,         N-methyl-N-(2-methylpentyl)aminosulfonyl,         N-methyl-N-(3-methylpentyl)aminosulfonyl,         N-methyl-N-(4-methylpentyl)aminosulfonyl,         N-methyl-N-(1,1-dimethylbutyl)aminosulfonyl,         N-methyl-N-(1,2-dimethylbutyl)aminosulfonyl,         N-methyl-N-(1,3-dimethylbutyl)aminosulfonyl,         N-methyl-N-(2,2-dimethylbutyl)aminosulfonyl,         N-methyl-N-(2,3-dimethylbutyl)aminosulfonyl,         N-methyl-N-(3,3-dimethylbutyl)aminosulfonyl,         N-methyl-N-(1-ethylbutyl)aminosulfonyl,         N-methyl-N-(2-ethylbutyl)aminosulfonyl,         N-methyl-N-(1,1,2-trimethylpropyl)aminosulfonyl,         N-methyl-N-(1,2,2-trimethylpropyl)aminosulfonyl,         N-methyl-N-(1-ethyl-1-methylpropyl)aminosulfonyl,         N-methyl-N-(1-ethyl-2-methylpropyl)aminosulfonyl,         N-ethyl-N-pentylaminosulfonyl,         N-ethyl-N-(1-methylbutyl)aminosulfonyl,         N-ethyl-N-(2-methylbutyl)aminosulfonyl,         N-ethyl-N-(3-methylbutyl)aminosulfonyl,         N-ethyl-N-(2,2-dimethypropyl)aminosulfonyl,         N-ethyl-N-(1,1-ethylpropyl)aminosulfonyl,         N-ethyl-N-hexylaminosulfonyl,         N-ethyl-N-(1,1-dimethylpropyl)aminosulfonyl,         N-ethyl-N-(1,2-dimethyl propyl)aminosulfonyl,         N-ethyl-N-(1-methylpentyl)aminosulfonyl,         N-ethyl-N-(2-methylpentyl)aminosulfonyl,         N-ethyl-N-(3-methylpentyl)aminosulfonyl,         N-ethyl-N-(4-methylpentyl)aminosulfonyl,         N-ethyl-N-(1,1-methylbutyl)aminosulfonyl,         N-ethyl-N-(1,2-dimethylbutyl)aminosulfonyl,         N-ethyl-N-(1,3-dimethylbutyl)aminosulfonyl,         N-ethyl-N-(2,2-dimethylbutyl)aminosulfonyl,         N-ethyl-N-(2,3-dimethylbutyl)aminosulfonyl,         N-ethyl-N-(3,3-dimethylbutyl)aminosulfonyl,         N-ethyl-N-(1-ethylbutyl) aminosulfonyl,         N-ethyl-N-(2-ethylbutyl)aminosulfonyl,         N-ethyl-N-(1,1,2-trimethylpropyl)aminosulfonyl,         N-ethyl-N-(1,2,2-trimethyl propyl)aminosulfonyl,         N-ethyl-N-(1-ethyl-1-meth ylpropyl)aminosulfonyl,         N-ethyl-N-(1-ethyl-2-methylpropyl)aminosulfonyl,         N-propyl-N-pentylaminosulfonyl, N-butyl-N-pentylaminosulfonyl,         N,N-dipentylaminosulfonyl, N-propyl-N-hexylaminosulfonyl,         N-butyl-N-hexylaminosulfonyl, N-pentyl-N-hexylaminosulfonyl or         N,N-dihexylaminosulfonyl;     -   di-(C₁–C₄-alkyl)amino and the dialkylamino radicals of:         di-(C₁–C₄-alkyl)amino-C₁–C₄-alkoxycarbonyl and         N-(di-C₁–C₄-alkylamino)imino-C₁–C₆-alkyl for example         N,N-dimethylamino, N,N-diethylamino, N,N-dipropylamino,         N,N-di-(1-methylethyl)amino, N,N-dibutylamino,         N,N-di-(1-methylpropyl)amino, N,N-di-(2-methylpropyl)amino,         N,N-di-(1,1-dimethylethyl)amino, N-ethyl-N-methylamino,         N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino,         N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino,         N-methyl-N-(2-methylpropyl)amino,         N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino,         N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino,         N-ethyl-N-(1-methylpropyl)amino,         N-ethyl-N-(2-methylpropyl)amino,         N-ethyl-N-(1,1-dimethylethyl)amino,         N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino,         N-(1-methylpropyl)-N-propylamino,         N-(2-methylpropyl)-N-propylamino,         N-(1,1-dimethylethyl)-N-propylamino,         N-butyl-N-(1-methylethyl)amino,         N-(1-methylethyl)-N-(1-methylpropyl)amino,         N-(1-methylethyl)-N-(2-methylpropyl)amino,         N-(1,1-dimethylethyl)-N-(1-methylethyl)amino,         N-butyl-N-(1-methylpropyl)amino,         N-butyl-N-(2-methylpropyl)amino,         N-butyl-N-(1,1-dimethylethyl)amino,         N-(1-methylpropyl)-N-(2-methylpropyl)amino,         N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino or         N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino;     -   di-(C₁–C₆-alkyl)amino, and the dialkylamino radicals of         di-(C₁–C₆-alkyl)amino-imino-C₁–C₆-alkyl: di-(C₁–C₄-alkyl)amino         as mentioned above, and also N,N-dipentylamino,         N,N-dihexylamino, N-methyl-N-pentylamino, N-ethyl-N-pentylamino,         N-methyl-N-hexylamino or N-ethyl-N-hexylamino;     -   C₁–C₄-alkylcarbonyl: for example methylcarbonyl, ethylcarbonyl,         propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl,         1-methylpropylcarbonyl, 2-methylpropylcarbonyl or         1,1-dimethylethylcarbonyl;     -   C₁–C₆-alkylcarbonyl, and the alkylcarbonyl radicals of         phenoxy-C₁–C₆-alkylcarbonyl,         heterocyclyloxy-C₁–C₆-alkylcarbonyl, C₁–C₆-alkylcarbonylamino,         C₁–C₆-alkylcarbonyl-C₁–C₆-alkyl: C₁–C₄-alkylcarbonyl, as         mentioned above, and also, for example, pentylcarbonyl,         1-methylbutylcarbonyl, 2-methylbutylcarbonyl,         3-methylbutylcarbonyl, 2,2-dimethylpropylcarbonyl,         1-ethylpropylcarbonyl, hexylcarbonyl,         1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl,         1-methylpentylcarbonyl, 2-methylpentylcarbonyl,         3-methylpentylcarbonyl, 4-methylpentylcarbonyl,         1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl,         1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl,         2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl,         1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl,         1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl,         l-ethyl-1-methylpropylcarbonyl or         1-ethyl-2-methylpropylcarbonyl;     -   C₁–C₂₀-alkylcarbonyl: C₁–C₆-alkylcarbonyl, as mentioned above,         and also heptylcarbonyl, octylcarbonyl, pentadecylcarbonyl or         heptadecylcarbonyl;     -   C₁–C₆-haloalkylcarbonyl: a C₁–C₆-alkylcarbonyl radical as         mentioned above which is partially or fully substituted by         fluorine, chlorine, bromine and/or iodine, i.e., for example,         chloroacetyl, dichloroacetyl, trichloroacetyl, fluoroacetyl,         difluoroacetyl, trifluoroacetyl, chlorofluoroacetyl,         dichlorofluoroacetyl, chlorodifluoroacetyl,         2-fluoroethylcarbonyl, 2-chloroethylcarbonyl,         2-bromoethylcarbonyl, 2-iodoethylcarbonyl,         2,2-difluoroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl,         2-chloro-2-fluoroethylcarbonyl,         2-chloro-2,2-fluoroethylcarbonyl,         2,2-dichloro-2-fluoroethylcarbonyl,         2,2,2-trichloroethylcarbonyl, pentafluoroethylcarbonyl,         2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl,         2,2-difluoropropylcarbonyl, 2,3-difluoropropylcarbonyl,         2-chloropropylcarbonyl, 3-chloropropylcarbonyl,         2,3-dichloropropylcarbonyl, 2-bromopropylcarbonyl,         3-bromopropylcarbonyl, 3,3,3-trifluoropropylcarbonyl,         3,3,3-trichloropropylcarbonyl,         2,2,3,3,3-pentafluoropropylcarbonyl, heptafluoropropylcarbonyl,         1-(fluoromethyl)-2-fluoroethylcarbonyl,         1-(chloromethyl)-2-chloroethylcarbonyl,         1-(bromomethyl)-2-bromoethylcarbonyl, 4-fluorobutylcarbonyl,         4-chlorobutylcarbonyl, 4-bromobutylcarbonyl,         nonafluorobutylcarbonyl, 5-fluoropentylcarbonyl,         5-chloropentylcarbonyl, 5-bromopentylcarbonyl,         Perfluoropentylcarbonyl, 6-fluorohexylcarbonyl,         6-chlorohexylcarbonyl, 6-bromohexylcarbonyl or         Perfluorohexylcarbonyl;     -   C₁–C₄-alkoxycarbonyl, and the alkoxycarbonyl moieties of         di-(C₁–C₄-alkyl)amino-C₁–C₄-alkoxycarbonyl, for example         methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl,         1-methylethoxycarbonyl, butoxycarbonyl, 1-methylpropoxycarbonyl,         2-methylpropoxycarbonyl or 1,1-dimethylethoxycarbonyl;     -   (C₁–C₆-alkoxy)carbonyl, and the alkoxycarbonyl moieties of         C₁–C₆-alkoxycarbonyloxy: (C₁–C₄-alkoxy)carbonyl, as mentioned         above, and also, for example, pentoxycarbonyl,         1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl,         3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl,         1-ethylpropoxycarbonyl, hexoxycarbonyl,         1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl,         1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl,         3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl,         1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl,         1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl,         2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl,         1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl,         1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl,         1-ethyl-1-methylpropoxycarbonyl or         1-ethyl-2-methylpropoxycarbonyl;     -   C₁–C₆-haloalkoxycarbonyl: a C₁–C₆-alkoxycarbonyl radical as         mentioned above which is partially or fully substituted by         fluorine, chlorine, bromine and/or iodine, i.e., for example,         fluoromethoxycarbonyl, difluoromethoxycarbonyl,         trifluoromethoxycarbonyl, chlorodifluoromethoxycarbonyl,         bromodifluoromethoxycarbonyl, 2-fluoroethoxycarbonyl,         2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl,         2-iodoethoxycarbonyl, 2,2-difluoroethoxycarbonyl,         2,2,2-trifluoroethoxycarbonyl, 2-chloro-2-fluoroethoxycarbonyl,         2-chloro-2,2-difluoroethoxycarbonyl,         2,2-dichloro-2-fluoroethoxycarbonyl,         2,2,2-trichloroethoxycarbonyl, pentafluoroethoxycarbonyl,         2-fluoropropoxycarbonyl, 3-fluoropropoxycarbonyl,         2-chloropropoxycarbonyl, 3-chloropropoxycarbonyl,         2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl,         2,2-difluoropropoxycarbonyl, 2,3-difluoropropoxycarbonyl,         2,3-dichloropropoxycarbonyl, 3,3,3-trifluoropropoxycarbonyl,         3,3,3-trichloropropoxycarbonyl,         2,2,3,3,3-pentafluoropropoxycarbonyl,         heptafluoropropoxycarbonyl,         1-(fluoromethyl)-2-fluoroethoxycarbonyl,         1-(chloromethyl)-2-chloroethoxycarbonyl,         1-(bromomethyl)-2-bromethoxycarbonyl, 4-fluorobutoxycarbonyl,         4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl,         4-iodobutoxycarbonyl, 5-fluoropentoxycarbonyl,         5-chloropentoxycarbonyl, 5-bromopentoxycarbonyl,         6-fluorohexoxycarbonyl, 6-chlorohexoxycarbonyl or         6-bromohexoxycarbonyl;     -   (C₁–C₄-alkyl)carbonyloxy: acetyloxy, ethylcarbonyloxy,         propylcarbonyloxy, 1-methylethylcarbonyloxy, butylcarbonyloxy,         1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy or         1,1-dimethylethylcarbonyloxy;     -   (C₁–C₄-alkylamino)carbonyl: for example methylaminocarbonyl,         ethylaminocarbonyl, propylaminocarbonyl,         1-methylethylaminocarbonyl, butylaminocarbonyl,         1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or         1,1-dimethylethylaminocarbonyl;     -   (C₁–C₆-alkylamino)carbonyl: (C₁–C₄-alkylamino)carbonyl, as         mentioned above, and also, for example, pentylaminocarbonyl,         1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl,         3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl,         1-ethylpropylaminocarbonyl, hexylaminocarbonyl,         1,1-dimethylpropylaminocarbonyl,         1,2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl,         2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl,         4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl,         1,2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl,         2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl,         3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl,         2-ethylbutylaminocarbonyl, 1,1,2-trimethylpropylaminocarbonyl,         1,2,2-trimethylpropylaminocarbonyl,         1-ethyl-1-methylpropylaminocarbonyl or         1-ethyl-2-methylpropylaminocarbonyl;     -   di-(C₁–C₄-alkyl)aminocarbonyl: for example         N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl,         N,N-di-(1-methylethyl)aminocarbonyl, N,N-dipropylaminocarbonyl,         N,N-dibutylaminocarbonyl, N,N-di-(1-methylpropyl)aminocarbonyl,         N,N-di-(2-methylpropyl)aminocarbonyl,         N,N-di-(1,1-dimethylethyl)aminocarbonyl,         N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl,         N-methyl-N-(1-methylethyl)aminocarbonyl,         N-butyl-N-methylaminocarbonyl,         N-methyl-N-(1-methylpropyl)aminocarbonyl,         N-methyl-N-(2-methylpropyl)aminocarbonyl,         N-(1,1-dimethylethyl)-N-methylaminocarbonyl,         N-ethyl-N-propylaminocarbonyl,         N-ethyl-N-(1-methylethyl)aminocarbonyl,         N-butyl-N-ethylaminocarbonyl,         N-ethyl-N-(1-methylpropyl)aminocarbonyl,         N-ethyl-N-(2-methylpropyl)aminocarbonyl,         N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl,         N-(1-methylethyl)-N-propylaminocarbonyl,         N-butyl-N-propylaminocarbonyl,         N-(1-methylpropyl)-N-propylaminocarbonyl,         N-(2-methylpropyl)-N-propylaminocarbonyl,         N-(1,1-dimethylethyl)-N-propylaminocarbonyl,         N-butyl-N-(1-methylethyl)aminocarbonyl,         N-(1-methylethyl)-N-(1-methylpropyl)aminocarbonyl,         N-(1-methylethyl)-N-(2-methylpropyl)aminocarbonyl,         N-(1,1-dimethylethyl)-N-(1-methylethyl)aminocarbonyl,         N-butyl-N-(1-methylpropyl) aminocarbonyl,         N-butyl-N-(2-methylpropyl)aminocarbonyl,         N-butyl-N-(1,1-dimethylethyl)aminocarbonyl,         N-(1-methylpropyl)-N-(2-methylpropyl)aminocarbonyl,         N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl or         N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl;     -   di-(C₁–C₆-alkyl)aminocarbonyl: di-(C₁–C₄-alkyl)aminocarbonyl as         mentioned above, and also, for example,         N-methyl-N-pentylaminocarbonyl,         N-methyl-N-(1-methylbutyl)aminocarbonyl,         N-methyl-N-(2-methylbutyl)aminocarbonyl,         N-methyl-N-(3-methylbutyl)aminocarbonyl,         N-methyl-N-(2,2-dimethylpropyl)aminocarbonyl,         N-methyl-N-(1-ethylpropyl)aminocarbonyl,         N-methyl-N-hexylaminocarbonyl,         N-methyl-N-(1,1-dimethylpropyl)aminocarbonyl,         N-methyl-N-(1,2-dimethylpropyl)aminocarbonyl,         N-methyl-N-(1-methylpentyl)aminocarbonyl,         N-methyl-N-(2-methylpentyl)aminocarbonyl,         N-methyl-N-(3-methylpentyl)aminocarbonyl,         N-methyl-N-(4-methylpentyl)aminocarbonyl,         N-methyl-N-(1,1-dimethylbutyl)aminocarbonyl,         N-methyl-N-(1,2-dimethylbutyl)aminocarbonyl,         N-methyl-N-(1,3-dimethylbutyl)aminocarbonyl,         N-methyl-N-(2,2-dimethylbutyl)aminocarbonyl,         N-methyl-N-(2,3-dimethylbutyl)aminocarbonyl,         N-methyl-N-(3,3-dimethylbutyl)aminocarbonyl,         N-methyl-N-(1-ethylbutyl)aminocarbonyl,         N-methyl-N-(2-ethylbutyl)aminocarbonyl,         N-methyl-N-(1,1,2-trimethylpropyl)aminocarbonyl,         N-methyl-N-(1,2,2-trimethylpropyl)aminocarbonyl,         N-methyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl,         N-methyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl,         N-ethyl-N-pentylaminocarbonyl,         N-ethyl-N-(1-methylbutyl)aminocarbonyl,         N-ethyl-N-(2-methylbutyl)aminocarbonyl,         N-ethyl-N-(3-methylbutyl)aminocarbonyl,         N-ethyl-N-(2,2-dimethylpropyl)aminocarbonyl,         N-ethyl-N-(1-ethylpropyl)aminocarbonyl,         N-ethyl-N-hexylaminocarbonyl,         N-ethyl-N-(1,1-dimethylpropyl)aminocarbonyl,         N-ethyl-N-(1,2-dimethylpropyl)aminocarbonyl,         N-ethyl-N-(1-methylpentyl)aminocarbonyl,         N-ethyl-N-(2-methylpentyl)aminocarbonyl,         N-ethyl-N-(3-methylpentyl)aminocarbonyl,         N-ethyl-N-(4-methylpentyl)aminocarbonyl,         N-ethyl-N-(1,1-dimethylbutyl)aminocarbonyl,         N-ethyl-N-(1,2-dimethylbutyl)aminocarbonyl,         N-ethyl-N-(1,3-dimethylbutyl)aminocarbonyl,         N-ethyl-N-(2,2-dimethylbutyl)aminocarbonyl,         N-ethyl-N-(2,3-dimethylbutyl)aminocarbonyl,         N-ethyl-N-(3,3-dimethylbutyl)aminocarbonyl,         N-ethyl-N-(1-ethylbutyl)aminocarbonyl,         N-ethyl-N-(2-ethylbutyl)aminocarbonyl,         N-ethyl-N-(1,1,2-trimethylpropyl)aminocarbonyl,         N-ethyl-N-(1,2,2-trimethylpropyl)aminocarbonyl,         N-ethyl-N-(1-ethyl-1-methylpropyl)aminocarbonyl,         N-ethyl-N-(1-ethyl-2-methylpropyl)aminocarbonyl,         N-Propyl-N-pentylaminocarbonyl, N-butyl-N-pentylaminocarbonyl,         N,N-dipentylaminocarbonyl, N-Propyl-N-hexylaminocarbonyl,         N-butyl-N-hexylaminocarbonyl, N-pentyl-N-hexylaminocarbonyl or         N,N-dihexylaminocarbonyl;     -   di-(C₁–C₆-alkyl)aminothiocarbonyl: for example         N,N-dimethylaminothiocarbonyl, N,N-diethylaminothiocarbonyl,         N,N-di-(1-methylethyl)aminothiocarbonyl,         N,N-dipropylaminothiocarbonyl, N,N-dibutylaminothiocarbonyl,         N,N-di-(1-methylpropyl)aminothiocarbonyl,         N,N-di-(2-methylpropyl)aminothiocarbonyl, N,         N-di-(1,1-dimethylethyl)aminothiocarbonyl,         N-ethyl-N-methylaminothiocarbonyl,         N-methyl-N-propylaminothiocarbonyl,         N-methyl-N-(1,1-methylethyl)aminothiocarbonyl,         N-butyl-N-methylaminothiocarbonyl,         N-methyl-N-(1-methyipropyl)aminothiocarbonyl,         N-methyl-N-(2-methyipropyl)aminothiocarbonyl,         N-(1,1-dimethylethyl)-N-methylaminothiocarbonyl,         N-ethyl-N-propylaminothiocarbonyl,         N-ethyl-N-(1-methylethyl)aminothiocarbonyl,         N-butyl-N-ethylaminothiocarbonyl,         N-ethyl-N-(1-methylpropyl)aminothiocarbonyl,         N-ethyl-N-(2-ethylpropyl)-aminothiocarbonyl,         N-ethyl-N-(1,1-dimethylethyl)-aminothiocarbonyl,         N-(1,1-methylethyl) N-propylaminothiocarbonyl,         N-butyl-N-propylaminothiocarbonyl,         N-(1-methylpropyl)-N-propylaminothiocarbonyl,         N-(2-methylpropyl)-N-propylaminothiocarbonyl,         N-(1,1-dimethylethyl)-N-propylaminothiocarbonyl,         N-butyl-N-(1,1-methylethyl)aminothiocarbonyl,         N-(1-methylethyl)-N-(1-methylpropyl)aminothiocarbonyl,         N-(1-methylethyl)-N-(2-methylpropyl) aminothiocarbonyl,         N-(1,1-dimethylethyl)-N-(1-methylethyl)aminothiocarbonyl,         N-butyl-N-(1-methylpropyl) aminothiocarbonyl,         N-butyl-N-(2-methylpropyl)aminothiocarbonyl,         N-butyl-N-(1,1-dimethylethyl)aminothiocarbonyl,         N-(1-methylpropyl)-N-(2-methylpropyl)aminothiocarbonyl,         N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminothiocarbonyl,         N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminothiocarbonyl,         N-methyl-N-pentylaminothiocarbonyl,         N-methyl-N-(1-methylbutyl)aminothiocarbonyl,         N-methyl-N-(2-methylbutyl) aminothiocarbonyl,         N-methyl-N-(3-methylbutyl)aminothiocarbonyl,         N-methyl-N-(2,2-dimethylpropyl)aminothiocarbonyl,         N-methyl-N-(1-ethylpropyl)aminothiocarbonyl,         N-methyl-N-hexylaminothiocarbonyl,         N-methyl-N-(1,1-dimethyipropyl) aminothiocarbonyl,         N-methyl-N-(1,2-dimethylpropyl)aminothiocarbonyl,         N-methyl-N-(1-methylpentyl) aminothiocarbonyl,         N-methyl-N-(2-methylpentyl)aminothiocarbonyl,         N-methyl-N-(3-methylpentyl)aminothiocarbonyl,         N-methyl-N-(4-methylpentyl)aminothiocarbonyl,         N-methyl-N-(1,1-dimethylbutyl)aminothiocarbonyl,         N-methyl-N-(1,2-dimethylbutyl)aminothiocarbonyl,         N-methyl-N-(1,3-dimethylbutyl)aminothiocarbonyl,         N-methyl-N-(2,2-dimethylbutyl)aminothiocarbonyl,         N-methyl-N-(2,3-dimethylbutyl) aminothiocarbonyl,         N-methyl-N-(3,3-dimethylbutyl)aminothiocarbonyl,         N-methyl-N-(1-ethylbutyl)aminothiocarbonyl,         N-methyl-N-(2-ethylbutyl)aminothiocarbonyl,         N-methyl-N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl,         N-methyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl,         N-methyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl,         N-methyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl,         N-ethyl-N-pentylaminothiocarbonyl,         N-ethyl-N-(1-methylbutyl)aminothiocarbonyl,         N-ethyl-N-(2-methylbutyl)aminothiocarbonyl,         N-ethyl-N-(3-methylbutyl)aminothiocarbonyl,         N-ethyl-N-(2,2-dimethylpropyl)aminothiocarbonyl,         N-ethyl-N-(1-ethylpropyl)aminothiocarbonyl,         N-ethyl-N-hexylaminothiocarbonyl,         N-ethyl-N-(1,1-dimethylpropyl)aminothiocarbonyl,         N-ethyl-N-(1,2-dimethylpropyl)aminothiocarbonyl,         N-ethyl-N-(1-methylpentyl)aminothiocarbonyl,         N-ethyl-N-(2-methylpentyl)aminothiocarbonyl,         N-ethyl-N-(3-methylpentyl)aminothiocarbonyl,         N-ethyl-N-(4-methylpentyl)aminothiocarbonyl,         N-ethyl-N-(1,1-dimethylbutyl)aminothiocarbonyl,         N-ethyl-N-(1,2-dimethylbutyl)aminothiocarbonyl,         N-ethyl-N-(1,3-dimethylbutyl)aminothiocarbonyl,         N-ethyl-N-(2,2-dimethylbutyl)aminothiocarbonyl,         N-ethyl-N-(2,3-dimethylbutyl)aminothiocarbonyl,         N-ethyl-N-(3,3-dimethylbutyl)aminothiocarbonyl,         N-ethyl-N-(1-ethylbutyl)aminothiocarbonyl,         N-ethyl-N-(2-ethylbutyl)aminothiocarbonyl,         N-ethyl-N-(1,1,2-trimethylpropyl)aminothiocarbonyl,         N-ethyl-N-(1,2,2-trimethylpropyl)aminothiocarbonyl,         N-ethyl-N-(1-ethyl-1-methylpropyl)aminothiocarbonyl,         N-ethyl-N-(1-ethyl-2-methylpropyl)aminothiocarbonyl,         N-Propyl-N-pentylaminothiocarbonyl,         N-butyl-N-pentylaminothiocarbonyl,         N,N-dipentylaminothiocarbonyl,         N-Propyl-N-hexylaminothiocarbonyl,         N-butyl-N-hexylaminothiocarbonyl,         N-pentyl-N-hexylaminothiocarbonyl or         N,N-dihexylaminothiocarbonyl;     -   C₁–C₄-alkoxy-C₁–C₄-alkyl: C₁–C₄-alkyl which is substituted by         C₁–C₄-alkoxy as mentioned above, i.e., for example,         methoxymethyl, ethoxymethyl, propoxymethyl,         (1-methylethoxy)methyl, butoxymethyl, (1-methylpropoxy)methyl,         (2-methylpropoxy)methyl, (1,1-dimethylethoxy)methyl,         2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(propoxy)ethyl,         2-(1-methylethoxy)ethyl, 2-(butoxy)ethyl,         2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl,         2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)-propyl,         2-(ethoxy)propyl, 2-(propoxy)propyl, 2-(1-methylethoxy)propyl,         2-(butoxy)propyl, 2-(1-methylpropoxy)propyl,         2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl,         3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(propoxy)propyl,         3-(1-methylethoxy)propyl, 3-(butoxy)propyl,         3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl,         3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl,         2-(propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(butoxy)butyl,         2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl,         2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl,         3-(propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(butoxy)butyl,         3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl,         3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl,         4-(propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(butoxy)butyl,         4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl or         4-(1,1-dimethylethoxy)butyl;     -   C₁–C₄-alkoxy-C₁–C₄-alkoxy, and the alkoxyalkoxy moieties of         C₁–C₄-alkoxy-C₁–C₄-alkoxycarbonyl: C₁–C₄-alkoxy which is         substituted by C₁–C₄-alkoxy as mentioned above, i.e., for         example, methoxymethoxy, ethoxymethoxy, propoxymethoxy,         (1-methylethoxy)methoxy, butoxymethoxy,         (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy,         (1,1-dimethylethoxy)methoxy, 2-(methoxy)ethoxy,         2-(ethoxy)ethoxy, 2-(propoxy)ethoxy, 2-(1-methylethoxy)ethoxy,         2-(butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy,         2-(2-methylpropoxy)ethoxy, 2-(1,1-dimethylethoxy)ethoxy,         2-(methoxy)propoxy, 2-(ethoxy)propoxy, 2-(propoxy)propoxy,         2-(1-methylethoxy)propoxy, 2-(butoxy)propoxy,         2-(1-methylpropoxy)propoxy, 2-(2-methylpropoxy)propoxy,         2-(1,1-dimethylethoxy)propoxy, 3-(methoxy)propoxy,         3-(ethoxy)propoxy, 3-(propoxy)propoxy,         3-(1-methylethoxy)propoxy, 3-(butoxy)propoxy,         3-(1-methylpropoxy)propoxy, 3-(2-methylpropoxy)propoxy,         3-(1,1-dimethylethoxy)propoxy, 2-(methoxy)butoxy,         2-(ethoxy)butoxy, 2-(propoxy)butoxy, 2-(1-methylethoxy)butoxy,         2-(butoxy)butoxy, 2-(1-methylpropoxy)butoxy,         2-(2-methylpropoxy)butoxy, 2-(1,1-dimethylethoxy)butoxy,         3-(methoxy)butoxy, 3-(ethoxy)butoxy, 3-(propoxy)butoxy,         3-(1-methylethoxy)butoxy, 3-(butoxy)butoxy,         3-(1-methylpropoxy)butoxy, 3-(2-methylpropoxy)butoxy,         3-(1,1-dimethylethoxy)butoxy, 4-(methoxy)butoxy,         4-(ethoxy)butoxy, 4-(propoxy)butoxy, 4-(1-methylethoxy)butoxy,         4-(butoxy)butoxy, 4-(1-methylpropoxy)butoxy,         4-(2-methylpropoxy)butoxy or 4-(1,1-dimethylethoxy)butoxy;     -   C₃–C₆-alkenyl, and the alkenyl moieties of         C₃–C₆-alkenylcarbonyl, C₃–C₆-alkenyloxy,         C₃–C₆-alkenyloxycarbonyl, C₃–C₆-alkenylaminocarbonyl,         N—(C₃–C₆-alkenyl)-N-(C₁–C₆alkyl) aminocarbonyl,         N—(C₃–C₆-alkenyl)-N-(C₁–C₆-alkoxy)aminocarbonyl: for example         prop-2-en-1-yl, but-1-en-4-yl, 1-methyl-prop-2-en-1-yl,         2-methylprop-2-en-1-yl, 2-buten-1-yl, 1-penten-3-yl,         1-penten-4-yl, 2-penten-4-yl, 1-methylbut-2-en-1-yl,         2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl,         1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl,         3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl,         1,2-dimethylprop-2-en-1-yl, 1-ethylprop-2-en-1-yl,         hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl,         1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl,         3-ethylpent-3-en-1-yl, 4-ethylpent-3-en-1-yl,         1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl,         3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl,         1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl,         1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl,         1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl,         2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-2-en-1-yl,         2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-2-en-1-yl,         2,3-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl,         2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl,         1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl or         1-ethyl-2-methylprop-2-en-1-yl;     -   C₂–C₆-alkenyl, and the alkenyl moieties of         C₂–C₆-alkenylcarbonyl, phenyl-C₂–C₆-alkenylcarbonyl and         heterocyclyl-C₂–C₆-alkenylcarbonyl: C₃–C₆-alkenyl as mentioned         above, and also ethenyl;     -   C₃–C₆-haloalkenyl: a C₃–C₆-alkenyl radical as mentioned above         which is partially or fully substituted by fluorine, chlorine,         bromine and/or iodine, i.e., for example, 2-chloroallyl,         3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl,         2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl,         3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl,         2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl;     -   C₃–C₆-alkynyl, and the alkyinyl moieties of         C₃–C₆-alkynylcarbonyl, C₃–C₆-alkynyloxy,         C₃–C₆-alkynyloxycarbonyl, C₃–C₆-alkynylaminocarbonyl,         N—(C₃–C₆-alkynyl)-N-(C₁–C₆-alkyl)aminocarbonyl,         N—(C₃–C₆-alkynyl)-N-(C₁–C₆-alkoxyaminocarbonyl: for example         propargyl, but-1-yn-3-yl, but-1-yn-4-yl, but-2-yn-1-yl,         pent-1-yn-3-yl, pent-1-yn-4-yl, pent-1-yn-5-yl, pent-2-yn-1-yl,         pent-2-yn-4-yl, pent-2-yn-5-yl, 3-methyl-but-1-yn-3-yl,         3-methylbut-1-yn-4-yl, hex-1-yn-3-yl, hex-1-yn-4-yl,         hex-1-yn-5-yl, hex-1-yn-6-yl, hex-2-yn-1-yl, hex-2-yn-4-yl,         hex-2-yn-5-yl, hex-2-yn-6-yl, hex-3-yn-1-yl, hex-3-yn-2-yl,         3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl,         3-methylpent-1-yn-5-yl, 4-methylpent-2-yn-4-yl or         4-methylpent-2-yn-5-yl;     -   C₂–C₆-alkynyl, and the alkynyl moieties of C₂–C₆alkynylcarbonyl:         C₃–C₆-alkynyl as mentioned above, and also ethynyl;     -   C₃–C₆-haloalkynyl: a C₃–C₆-alkynyl radical as mentioned above         which is partially or fully substitued by fluorine, chlorine,         bromine and/or iodine, i.e., for example,         1,1-difluoroprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl,         4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl,         1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl,         5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl,         6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl;     -   C₃–C₆-cycloalkyl, and the cycloalkyl moieties of         C₃–C₆-cycloalkylcarbonyl: for example cyclopropyl, cyclobutyl,         cyclopentyl or cyclohexyl;     -   heterocyclyl, and the heterocyclyl moieties of         heterocyclylcarbonyl, heterocyclyl-C₁–C₆-alkyl, heterocyclyloxy,         heterocyclylthio, heterocyclyloxyalkylcarbonyl,         heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl,         heterocyclylcarbonyl-C₁–C₆-alkyl,         N—(C₁–C₆-alkyl)-N-(heterocyclyl)aminocarbonyl,         heterocyclylaminocarbonyl: a saturated, partially saturated or         unsaturated 5- or 6-membered heterocyclic ring which is attached         via a carbon and has one to four identical or different hetero         atoms selected from the following group: oxygen, sulfur or         nitrogen, i.e., for example, 5-membered rings having a hetero         atom such as, for example: tetrahydrofuran-2-yl,         tetrahydrofuran-3-yl, tetrahydrothien-2-yl,         tetrahydrothien-3-yl, tetrahydropyrrol-2-yl,         tetrahydropyrrol-3-yl, 2,3-dihydrofuran-2-yl,         2,3-dihydrofuran-3-yl, 2,5-dihydrofuran-2-yl,         2,5-dihydrofuran-3-yl, 4,5-dihydrofuran-2-yl,         4,5-dihydrofuran-3-yl, 2,3-dihydrothien-2-yl,         2,3-dihydrothien-3-yl, 2,5-dihydrothien-2-yl,         2,5-dihydrothien-3-yl, 4,5-dihydrothien-2-yl,         4,5-dihydrothien-3-yl, 2,3-dihydro-1H-pyrrol-2-yl,         2,3-dihydro-1H-pyrrol-3-yl, 2,5-dihydro-1H-pyrrol-2-yl,         2,5-dihydro-1H-pyrrol-3-yl, 4,5-dihydro-1H-pyrrol-2-yl,         4,5-dihydro-1H-pyrrol-3-yl, 3,4-dihydro-2H-pyrrol-2-yl,         3,4-dihydro-2H-pyrrol-3-yl, 3,4-dihydro-5H-pyrrol-2-yl,         3,4-dihydro-5H-pyrrol-3-yl, 2-furyl, 3-furyl, 2-thienyl,         3-thienyl, pyrrol-2-yl or pyrrol-3-yl;

5-membered rings having two hetero atoms such as, for example,

-   tetrahydropyrazol-3-yl, tetrahydropyrazol-3-yl,     tetrahydropyrazol-4-yl, tetrahydroisoxazol-3-yl,     tetrahydroisoxazol-4-yl, tetrahydroisoxazol-5-yl,     1,2-oxathiolan-3-yl, 1,2-oxathiolan-4-yl, 1,2-oxathiolan-5-yl,     tetrahydroisothiazol-3-yl, tetrahydroisothiazol-4-yl,     tetrahydroisothiazol-5-yl, 1,2-dithiolan-3-yl, 1,2-dithiolan-4-yl,     tetrahydroimidazol-2-yl, tetrahydroimidazol-4-yl,     tetrahydrooxazol-2-yl, tetrahydrooxazol-4-yl, tetrahydrooxazol-5-yl,     tetrahydrothiazol-2-yl, tetrahydrothiazol-4-yl,     tetrahydrothiazol-5-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl,     1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl,     1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, 4,5-dihydro-1H-pyrazol-3-yl,     4,5-dihydro-1H-pyrazol-4-yl, 4,5-dihydro-1H-pyrazol-5-yl,     2,5-dihydro-1H-pyrazol-3-yl, 2,5-dihydro-1H-pyrazol-4-yl,     2,5-dihydro-1H-pyrazol-5-yl, 4,5-dihydroisoxazol-3-yl,     4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl,     2,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-4-yl,     2,5-dihydroisoxazol-5-yl, 2,3-dihydroisoxazol-3-yl,     2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl,     4,5-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl,     4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-3-yl,     2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5-yl,     2,3-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-4-yl,     2,3-dihydroisothiazol-5-yl, Δ³-1,2-dithiol-3-yl,     Δ³-1,2-dithiol-4-yl, Δ³-1,2-dithiol-5-yl,     4,5-dihydro-1H-imidazol-2-yl, 4,5-dihydro-1H-imidazol-4-yl,     4,5-dihydro-1H-imidazol-5-yl, 2,5-dihydro-1H-imidazol-2-yl,     2,5-dihydro-1H-imidazol-4-yl, 2,5-dihydro-1H-imidazol-5-yl,     2,3-dihydro-1H-imidazol-2-yl, 2,3-dihydro-1H-imidazol-4-yl,     4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl,     4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl,     2,5-dihydrooxazol-4-yl, 2,5-dihydrooxazol-5-yl,     2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-4-yl,     2,3-dihydrooxazol-5-yl, 4,5-dihydrothiazol-2-yl,     4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5-yl,     2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl,     2,5-dihydrothiazol-5-yl, 2,3-dihydrothiazol-2-yl,     2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 1,3-dioxol-2-yl,     1,3-dioxol-4-yl, 1,3-dithiol-2-yl, 1,3-dithiol-4-yl,     1,3-oxathiol-2-yl, 1,3-oxathiol-4-yl, 1,3-oxathiol-5-yl,     pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl,     isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl,     imidazol-2-yl, imidazol-4-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl,     thiazol-2-yl, thiazol-4-yl or thiazol-5-yl;

5-membered rings having 3 hetero atoms such as, for example,

-   1,2,3-Δ²-oxadiazolin-4-yl, 1,2,3-Δ²-oxadiazolin-5-yl,     1,2,4-Δ⁴-oxadiazolin-3-yl, 1,2,4-Δ⁴-oxadiazolin-5-yl,     1,2,4-Δ²-oxadiazolin-3-yl, 1,2,4-Δ²-oxadiazolin-5-yl,     1,2,4-Δ³-oxadiazolin-3-yl, 1,2,4-Δ³-oxadiazolin-5-yl,     1,3,4-Δ²-oxadiazolin-2-yl, 1,3,4-Δ²-oxadiazolin-5-yl,     1,3,4-Δ³-oxadiazolin-2-yl, 1,3,4-oxadiazolin-2-yl,     1,2,4-Δ⁴-thiadiazolin-3-yl, 1,2,4-Δ⁴-thiadiazolin-5-yl,     1,2,4-Δ³-thiadiazolin-3-yl, 1,2,4-Δ³-thiadiazolin-5-yl,     1,2,4-Δ²-thiadiazolin-3-yl, 1,2,4-Δ²-thiadiazolin-5-yl,     1,2,4-Δ²-thiadiazolin-2-yl, 1,3,4-Δ²-thiadiazolin-5-yl,     1,3,4-Δ³-thiadiazolin-2-yl, 1,3,4-thiadiazolin-2-yl,     1,3,2-dioxathiolan-4-yl, 1,2,3-Δ²-triazolin-4-yl,     1,2,3-Δ²-triazolin-5-yl, 1,2,4-Δ²-triazolin-3-yl,     1,2,4-Δ²-triazolin-5-yl, 1,2,4-Δ³-triazolin-3-yl,     1,2,4-Δ³-triazolin-5-yl, 1,2,4-Δ¹-triazolin-2-yl,     1,2,4-triazolin-3-yl, 3H-1,2,4-dithiazol-5-yl,     2H-1,3,4-dithiazol-5-yl, 2H-1,3,4-oxathiazol-5-yl,     1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,4-oxadiazol-3-yl,     1,2,4,-oxadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-thiadiazol-4-yl,     1,2,3-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,     1,3,4-thiadiazolyl-2-yl, 1,2,3-triazol-4-yl or 1,2,4-triazol-3-yl;

5-membered rings having 4 hetero atoms such as, for example, tetrazol-5-yl,

6-membered rings having 1 hetero atom such as, for example:

-   tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl,     piperidin-2-yl, piperidin-3-yl, piperidin-4-yl,     tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl,     tetrahydrothiopyran-4-yl, 2H-3,4-dihydropyran-6-yl,     2H-3,4-dihydropyran-5-yl, 2H-3,4-dihydropyran-4-yl,     2H-3,4-dihydropyran-3-yl, 2H-3,4-dihydropyran-2-yl,     2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydrothiopyran-5-yl,     2H-3,4-dihydrothiopyran-4-yl, 2H-3,4-dihydropyran-3-yl,     2H-3,4-dihydropyran-2-yl, 1,2,3,4-tetrahydropyridin-6-yl,     1,2,3,4-tetrahydropyridin-5-yl, 1,2,3,4-tetrahydropyridin-4-yl,     1,2,3,4-tetrahydropyridin-3-yl, 1,2,3,4-tetrahydropyridin-2-yl,     2H-5,6-dihydropyran-2-yl, 2H-5,6-dihydropyran-3-yl,     2H-5,6-dihydropyran-4-yl, 2H-5,6-dihydropyran-5-yl,     2H-5,6-dihydropyran-6-yl, 2H-5,6-dihydropyran-5-yl,     2H-5,6-dihydrothiopyran-6-yl, 2H-5,6-dihydrothiopyran-2-yl,     2H-5,6-dihydrothiopyran-3-yl, 2H-5,6-dihydrothiopyran-4-yl,     2H-5,6-dihydrothiopyran-5-yl, 2H-5,6-dihydrothiopyran-6-yl,     1,2,5,6-tetrahydropyridin-2-yl, 1,2,5,6-tetrahydropyridin-3-yl,     1,2,5,6-tetrahydropyridin-4-yl, 1,2,5,6-tetrahydropyridin-5-yl,     1,2,5,6-tetrahydropyridin-6-yl, 2,3,4,5-tetrahydropyridin-2-yl,     2,3,4,5-tetrahydropyridin-3-yl, 2,3,4,5-tetrahydropyridin-4-yl,     2,3,4,5-tetrahydropyridin-5-yl, 2,3,4,5-tetrahydropyridin-6-yl,     4H-pyran-2-yl, 4H-pyran-3-yl, 4H-pyran-4-yl, 4H-thiopyran-2-yl,     4H-thiopyran-3-yl, 4H-thiopyran-4-yl, 1,4-dihydropyridin-2-yl,     1,4-dihydropyridin-3-yl, 1,4-dihydropyridin-4-yl, 2H-pyran-2-yl,     2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl,     2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl,     2H-thiopyran-5-yl, 2H-thiopyran-6-yl, 1,2-dihydropyridin-2-yl,     1,2-dihydropyridin-3-yl, 1,2-dihydropyridin-4-yl,     1,2-dihydropyridin-5-yl, 1,2-dihydropyridin-6-yl,     3,4-dihydropyridin-2-yl, 3,4-dihydropyridin-3-yl,     3,4-dihydropyridin-4-yl, 3,4-dihydropyridin-5-yl,     3,4-dihydropyridin-6-yl, 2,5-dihydropyridin-2-yl,     2,5-dihydropyridin-3-yl, 2,5-dihydropyridin-4-yl,     2,5-dihydropyridin-5-yl, 2,5-dihydropyridin-6-yl,     2,3-dihydropyridin-2-yl, 2,3-dihydropyridin-3-yl,     2,3-dihydropyridin-4-yl, 2,3-dihydropyridin-5-yl,     2,3-dihydropyridin-6-yl, pyridin-2-yl, pyridin-3-yl or pyridin-4-yl; -   6-membered rings having 2 hetero atoms such as, for example, -   1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl,     1,3-dithian-2-yl, 1,3-dithian-4-yl, 1,3-dithian-5-yl,     1,4-dithian-2-yl, 1,3-oxathian-2-yl, 1,3-oxathian-4-yl,     1,3-oxathian-5-yl, 1,3-oxathian-6-yl, 1,4-oxathian-2-yl,     1,4-oxathian-3-yl, 1,2-dithian-3-yl, 1,2-dithian-4-yl,     hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl,     hexahydropyrimidin-5-yl, hexahydropyrazin-2-yl,     hexahydropyridazin-3-yl, hexahydropyridazin-4-yl,     tetrahydro-1,3-oxazin-2-yl, tetrahydro-1,3-oxazin-4-yl,     tetrahydro-1,3-oxazin-5-yl, tetrahydro-1,3-oxazin-6-yl,     tetrahydro-1,3-thiazin-2-yl, tetrahydro-1,3-thiazin-4-yl,     tetrahydro-1,3-thiazin-5-yl, tetrahydro-1,3-thiazin-6-yl,     tetrahydro-1,4-thiazin-2-yl, tetrahydro-1,4-thiazin-3-yl,     tetrahydro-1,4-oxazin-2-yl, tetrahydro-1,4-oxazin-3-yl,     tetrahydro-1,2-oxazin-3-yl, tetrahydro-1,2-oxazin-4-yl,     tetrahydro-1,2-oxazin-5-yl, tetrahydro-1,2-oxazin-6-yl,     2H-5,6-dihydro-1,2-oxazin-3-yl, 2H-5,6-dihydro-1,2-oxazin-4-yl,     2H-5,6-dihydro-1,2-oxazin-5-yl, 2H-5,6-dihydro-1,2-oxazin-6-yl,     2H-5,6-dihydro-1,2-thiazin-3-yl, 2H-5,6-dihydro-1,2-thiazin-4-yl,     2H-5,6-dihydro-1,2-thiazin-5-yl, 2H-5,6-dihydro-1,2-thiazin-6-yl,     4H-5,6-dihydro-1,2-oxazin-3-yl, 4H-5,6-dihydro-1,2-oxazin-4-yl,     4H-5,6-dihydro-1,2-oxazin-5-yl, 4H-5,6-dihydro-1,2-oxazin-6-yl,     4H-5,6-dihydro-1,2-thiazin-3-yl, 4H-5,6-dihydro-1,2-thiazin-4-yl,     4H-5,6-dihydro-1,2-thiazin-5-yl, 4H-5,6-dihydro-1,2-thiazin-6-yl,     2H-3,6-dihydro-1,2-oxazin-3-yl, 2H-3,6-dihydro-1,2-oxazin-4-yl,     2H-3,6-dihydro-1,2-oxazin-5-yl, 2H-3,6-dihydro-1,2-oxazin-6-yl,     2H-3,6-dihydro-1,2-thiazin-3-yl, 2H-3,6-dihydro-1,2-thiazin-4-yl,     2H-3,6-dihydro-1,2-thiazin-5-yl, 2H-3,6-dihydro-1,2-thiazin-6-yl,     2H-3,4-dihydro-1,2-oxazin-3-yl, 2H-3,4-dihydro-1,2-oxazin-4-yl,     2H-3,4-dihydro-1,2-oxazin-5-yl, 2H-3,4-dihydro-1,2-oxazin-6-yl,     2H-3,4-dihydro-1,2-thiazin-3-yl, 2H-3,4-dihydro-1,2-thiazin-4-yl,     2H-3,4-dihydro-1,2-thiazin-5-yl, 2H-3,4-dihydro-1,2-thiazin-6-yl,     2,3,4,5-tetrahydropyridazin-3-yl, 2,3,4,5-tetrahydropyridazin-4-yl,     2,3,4,5-tetrahydropyridazin-5-yl, 2,3,4,5-tetrahydropyridazin-6-yl,     3,4,5,6-tetrahydropyridazin-3-yl, 3,4,5,6-tetrahydropyridazin-4-yl,     1,2,5,6-tetrahydropyridazin-3-yl, 1,2,5,6-tetrahydropyridazin-4-yl,     1,2,5,6-tetrahydropyridazin-5-yl, 1,2,5,6-tetrahydropyridazin-6-yl,     1,2,3,6-tetrahydropyridazin-3-yl, 1,2,3,6-tetrahydropyridazin-4-yl,     4H-5,6-dihydro-1,3-oxazin-2-yl, 4H-5,6-dihydro-1,3-oxazin-4-yl,     4H-5,6-dihydro-1,3-oxazin-5-yl, 4H-5,6-dihydro-1,3-oxazin-6-yl,     4H-5,6-dihydro-1,3-thiazin-2-yl, 4H-5,6-dihydro-1,3-thiazin-4-yl,     4H-5,6-dihydro-1,3-thiazin-5-yl, 4H-5,6-dihydro-1,3-thiazin-6-yl,     3,4,5,6-tetrahydropyrimidin-2-yl, 3,4,5,6-tetrahydropyrimidin-4-yl,     3,4,5,6-tetrahydropyrimidin-5-yl, 3,4,5,6-tetrahydropyrimidin-6-yl,     1,2,3,4-tetrahydropyrazin-2-yl, 1,2,3,4-tetrahydropyrazin-5-yl,     1,2,3,4-tetrahydropyrimidin-2-yl, 1,2,3,4-tetrahydropyrimidin-4-yl,     1,2,3,4-tetrahydropyrimidin-5-yl, 1,2,3,4-tetrahydropyrimidin-6-yl,     2,3-dihydro-1,4-thiazin-2-yl, 2,3-dihydro-1,4-thiazin-3-yl,     2,3-dihydro-1,4-thiazin-5-yl, 2,3-dihydro-1,4-thiazin-6-yl,     2H-1,2-oxazin-3-yl, 2H-1,2-oxazin-4-yl, 2H-1,2-oxazin-5-yl,     2H-1,2-oxazin-6-yl, 2H-1,2-thiazin-3-yl, 2H-1,2-thiazin-4-yl,     2H-1,2-thiazin-5-yl, 2H-1,2-thiazin-6-yl, 4H-1,2-oxazin-3-yl,     4H-1,2-oxazin-4-yl, 4H-1,2-oxazin-5-yl, 4H-1,2-oxazin-6-yl,     4H-1,2-thiazin-3-yl, 4H-1,2-thiazin-4-yl, 4H-1,2-thiazin-5-yl,     4H-1,2-thiazin-6-yl, 6H-1,2-oxazin-3-yl, 6H-1,2-oxazin-4-yl,     6H-1,2-oxazin-5-yl, 6H-1,2-oxazin-6-yl, 6H-1,2-thiazin-3-yl,     6H-1,2-thiazin-4-yl, 6H-1,2-thiazin-5-yl, 6H-1,2-thiazin-6-yl,     2H-1,3-oxazin-2-yl, 2H-1,3-oxazin-4-yl, 2H-1,3-oxazin-5-yl,     2H-1,3-oxazin-6-yl, 2H-1,3-thiazin-2-yl, 2H-1,3-thiazin-4-yl,     2H-1,3-thiazin-5-yl, 2H-1,3-thiazin-6-yl, 4H-1,3-oxazin-2-yl,     4H-1,3-oxazin-4-yl, 4H-1,3-oxazin-5-yl, 4H-1,3-oxazin-6-yl,     4H-1,3-thiazin-2-yl, 4H-1,3-thiazin-4-yl, 4H-1,3-thiazin-5-yl,     4H-1,3-thiazin-6-yl, 6H-1,3-oxazin-2-yl, 6H-1,3-oxazin-4-yl,     6H-1,3-oxazin-5-yl, 6H-1,3-oxazin-6-yl, 6H-1,3-thiazin-2-yl,     6H-1,3-oxazin-4-yl, 6H-1,3-oxazin-5-yl, 6H-1,3-thiazin-6-yl,     2H-1,4-oxazin-2-yl, 2H-1,4-oxazin-3-yl, 2H-1,4-oxazin-5-yl,     2H-1,4-oxazin-6-yl, 2H-1,4-thiazin-2-yl, 2H-1,4-thiazin-3-yl,     2H-1,4-thiazin-5-yl, 2H-1,4-thiazin-6-yl, 4H-1,4-oxazin-2-yl,     4H-1,4-oxazin-3-yl, 4H-1,4-thiazin-2-yl, 4H-1,4-thiazin-3-yl,     1,4-dihydropyridazin-3-yl, 1,4-dihydropyridazin-4-yl,     1,4-dihydropyridazin-5-yl, 1,4-dihydropyridazin-6-yl,     1,4-dihydropyrazin-2-yl, 1,2-dihydropyrazin-2-yl,     1,2-dihydropyrazin-3-yl, 1,2-dihydropyrazin-5-yl,     1,2-dihydropyrazin-6-yl, 1,4-dihydropyrimidin-2-yl,     1,4-dihydropyrimidin-4-yl, 1,4-dihydropyrimidin-5-yl,     1,4-dihydropyrimidin-6-yl, 3,4-dihydropyrimidin-2-yl,     3,4-dihydropyrimidin-4-yl, 3,4-dihydropyrimidin-5-yl or     3,4-dihydropyrimidin-6-yl, pyridazin-3-yl, pyridazin-4-yl,     pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl or pyrazin-2-yl;

6-membered rings having 3 hetero atoms such as, for example,

-   1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl or     1,2,4-triazin-6-yl;

6-membered rings having 4 hetero atoms such as, for example,

-   1,2,4,5-tetrazin-3-yl;     where, if appropriate, the sulfur of the abovementioned heterocycles     may be oxidized to S=o or S(═O)₂;     and where a bicyclic ring system may be formed with a fused-on     phenyl ring or with a C₃–C₆-carbocycle or with another 5- to     6-membered heterocycle.     -   N-linked heterocyclyl: a saturated, partially saturated or         unsaturated 5- or 6-membered heterocyclic ring which is attached         via nitrogen and which contains at least one nitrogen and         optionally one to three identical or different hetero atoms         selected from the following group: oxygen, sulfur or nitrogen,         i.e., for example,

5-membered rings having 1 hetero atom which are linked by a nitrogen, such as, for example,

-   tetrahydropyrrol-1-yl, 2,3-dihydro-1H-pyrrol-1-yl,     2,5-dihydro-1H-pyrrol-1-yl or pyrrol-1-yl;

5-membered rings having 2 hetero atoms which are linked by a nitrogen such as, for example,

-   tetrahydropyrazol-1-yl, tetrahydroisoxazol-2-yl,     tetrahydroisothiazol-2-yl, tetrahydroimidazol-1-yl,     tetrahydrooxazol-3-yl, tetrahydrothiazol-3-yl,     4,5-dihydro-1H-pyrazol-1-yl, 2,5-dihydro-1H-pyrazol-1-yl,     2,3-dihydro-1H-pyrazol-1-yl, 2,5-dihydroisoxazol-2-yl,     2,3-dihydroisoxazol-2-yl, 2,5-dihydroisothiazol-2-yl,     2,3-dihydroisoxazol-2-yl, 4,5-dihydro-1H-imidazol-1-yl,     2,5-dihydro-1H-imidazol-1-yl, 2,3-dihydro-1H-imidazol-1-yl,     2,3-dihydrooxazol-3-yl, 2,3-dihydrothiazol-3-yl, pyrazol-1-yl or     imidazol-1-yl;

5-membered rings having 3 hetero atoms which are linked by a nitrogen such as, for example,

-   1,2,4-Δ⁴-oxadiazolin-2-yl, 1,2,4-Δ²-oxadiazolin-4-yl,     1,2,4-Δ³-oxadiazolin-2-yl, 1,3,4-Δ²-oxadiazolin-4-yl,     1,2,4-Δ²-thiadiazolin-2-yl, 1,2,4-Δ³-thiadiazolin-2-yl,     1,2,4-Δ²-thiadiazolin-4-yl, 1,3,4-Δ²-thiadiazolin-4-yl,     1,2,3-Δ²-triazolin-1-yl, 1,2,4-Δ²-triazolin-1-yl,     1,2,4-Δ²-triazolin-4-yl, 1,2,4-Δ³-triazolin-1-yl,     1,2,4-Δ¹-triazolin-4-yl, 1,2,3-triazol-1-yl or 1,2,4-triazol-1-yl;

5-membered rings having 4 hetero atoms which are linked by a nitrogen such as, for example,

-   tetrazol-1-yl;     and 6-membered rings having 1 hetero atom which are linked by a     nitrogen, such as, for example -   piperidin-1-yl, 1,2,3,4-tetrahydropyridin-1-yl,     1,2,5,6-tetrahydropyridin-1-yl, 1,4-dihydropyridin-1-yl or     1,2-dihydropyridin-1-yl;

6-membered rings having 2 hetero atoms which are linked by a nitrogen such as, for example,

-   hexahydropyrimidin-1-yl, hexahydropyrazin-1-yl,     hexahydropyridazin-1-yl, tetrahydro-1,3-oxazin-3-yl,     tetrahydro-1,3-thiazin-3-yl, tetrahydro-1,4-thiazin-4-yl,     tetrahydro-1,4-oxazin-4-yl, tetrahydro-1,2-oxazin-2-yl,     2H-5,6-dihydro-1,2-oxazin-2-yl, 2H-5,6-dihydro-1,2-thiazin-2-yl,     2H-3,6-dihydro-1,2-oxazin-2-yl,     2H-3,6-dihydro-1,2-thiazin-oxazin-2-yl,     2H-3,4-dihydro-1,2-thiazin-2-yl, 2,3,4,5-tetrahydropyridazin-2-yl,     1,2,5,6-tetrahydropyridazin-1-yl, 1,2,5,6-tetrahydropyridazin-2-yl,     1,2,3,6-tetrahydropyridazin-1-yl, 3,4,5,6-tetrahydropyrimidin-3-yl,     1,2,3,4-tetrahydropyrazin-1-yl, 1,2,3,4-tetrahydropyrimidin-1-yl,     1,2,3,4-tetrahydropyrimidin-3-yl, 2,3-dihydro-1,4-thiazin-4-yl,     2H-1,2-oxazin-2-yl, 2H-1,2-thiazin-2-yl, 4H-1,4-oxazin-4-yl,     4H-1,4-thiazin-4-yl, 1,4-dihydropyridazin-1-yl,     1,4-dihydropyrazin-1-yl, 1,2-dihydropyrazin-1-yl,     1,4-dihydropyrimidin-1-yl or 3,4-dihydropyrimidin-3-yl, and also     cyclic imides which are linked via nitrogen, such as:     -   phthalimide, tetrahydrophthalimide, succinimide, maleimide or         glutarimide, and also 4-oxo-1,4-dihydropyridin-1-yl.

All phenyl rings or heterocyclyl radicals, and also all phenyl components in phenyl-C₁–C₆-alkyl, phenylcarbonyl-C₁–C₆-alkyl, phenoxy, phenylthio, phenylcarbonyl, phenylalkenylcarbonyl, phenoxycarbonyl, phenoxyalkylcarbonyl, phenylaminocarbonyl and N—(C₁–C₆-alkyl)-N-phenylaminocarbonyl or heterocyclyl components in heterocyclyl-C₁–C₆-alkyl, heterocyclylcarbonyl-C₁–C₆-alkyl, heterocyclyloxy, heterocyclylthio, heterocyclylcarbonyl, heterocyclylalkenylcarbonyl, heterocyclyloxyalkylcarbonyl, heterocyclyloxycarbonyl, heterocyclylaminocarbonyl and N—(C₁–C₆-alkyl)-N-heterocyclylaminocarbonyl are, unless stated otherwise, preferably unsubstituted, or they carry one to three halogen atoms and/or one nitro group, one cyano radical and/or one or two methyl, trifluoromethyl, methoxy or trifluoromethoxy substituents.

The compounds of the formula I according to the invention where R⁴=IIa are referred to as compounds of the formula Ia, and compounds of the formula I where R⁴=IIb are referred to as Ib.

The compounds of the formula I should be particularly emphasized, where

-   R⁷ is C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-haloalkenyl, C₃–C₆-alkynyl,     C₃–C₆-haloalkynyl, C₃–C₆-Cycloalkyl, C₁–C₂₀-alkylcarbonyl,     C₂–C₆-alkenylcarbonyl, C₂–C₆-alkynylcarbonyl,     C₃–C₆-cycloalkylcarbonyl, C₁–C₆-alkoxycarbonyl,     C₃–C₆-alkenyloxycarbonyl, C₃–C₆-alkynyloxycarbonyl,     C₁–C₆-alkylthiocarbonyl, C₁–C₆-alkylaminocarbonyl,     C₃–C₆-alkenylaminocarbonyl, C₃–C₆-alkynylaminocarbonyl,     N,N-di-(C₁–C₆-alkyl)-aminocarbonyl,     N—(C₃–C₆-alkenyl)-N-(C₁–C₆-alkyl)aminocarbonyl,     N—(C₃–C₆-alkynyl)-N-(C₁–C₆-alkyl)aminocarbonyl,     N—(C₁–C₆-alkoxy)-N-(C₁–C₆-alkyl)aminocarbonyl,     N—(C₃–C₆-alkenyl)-N-(C₁–C₆-alkoxy)aminocarbonyl,     N—(C₃–C₆-alkynyl)-N-(C₁–C₆-alkoxy)-aminocarbonyl,     di-(C₁–C₆-alkyl)aminothiocarbonyl, C₁–C₆-alkylcarbonyl-C₁–C₆-alkyl,     C₁–C₆-alkoxyimino-C₁–C₆-alkyl, N—(C₁–C₆-alkylamino)imino-C₁–C₆-alkyl     or N,N-di-(C₁–C₆-alkylamino)imino-C₁–C₆-alkyl, where the alkyl,     cycloalkyl and alkoxy radicals mentioned may be partially or fully     halogenated and/or may carry one to thre of the following groups:     -   cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio, di-(C₁–C₄-alkyl)amino,         C₁–C₄-alkylcarbonyl, C₁–C₄-alkoxycarbonyl,         C₁–C₄-alkoxy-C₁–₄-alkoxycarbonyl,         di-(C₁–C₄-alkyl)amino-C₁–C₄-alkoxycarbonyl, hydroxycarbonyl,         C₁–C₄-alkylaminocarbonyl, di-(C₁–C₄-alkyl)aminocarbonyl,         aminocarbonyl, C₁–C₄-alkylcarbonyloxy or C₃–C₆-cycloalkyl;     -   phenyl, heterocyclyl, phenyl-C₁–C₆-alkyl,         heterocyclyl-C₁–C₆-alkyl, phenylcarbonyl-C₁–C₆-alkyl,         heterocyclylcarbonyl-C₁–C₆-alkyl, phenylcarbonyl,         heterocyclylcarbonyl, phenoxycarbonyl, heterocyclyloxycarbonyl,         phenoxythiocarbonyl, heterocyclyloxythiocarbonyl,         phenoxy-C₁–C₆-alkylcarbonyl, heterocyclyloxy-C₁–C₆alkylcarbonyl,         phenylaminocarbonyl, N—(C₁–C₆-alkyl)-N-(phenyl)aminocarbonyl,         heterocyclylaminocarbonyl,         N—(C₁–C₆-alkyl)-N-(heterocyclyl)aminocarbonyl,         phenyl-C₂–C₆-alkenylcarbonyl or         heterocyclyl-C₂–C₆-alkenylcarbonyl, where the phenyl and the         heterocyclyl radical of the 20 last-mentioned substituents may         be partially or fully halogenated and/or may carry one to three         of the following radicals:     -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or         C₁–C₄-haloalkoxy;

With a view to the use of the compounds of the formula I according to the invention as herbicides, the variables preferably have the following meanings, in each case on their own or in combination:

-   R¹ is nitro, halogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₁–C₆-alkoxy,     C₁–C₆-haloalkoxy, C₁–C₆-alkylthio, C₁–C₆-haloalkylthio,     C₁–C₆-alkylsulfonyl or C₁–C₆-haloalkylsulfonyl; -   R², R³ are hydrogen, C₁–C₆-alkyl or halogen; -   R⁴ is a compound of IIa or IIb

where

-   R⁵ is halogen, OR⁷, SR⁷, SO₂R⁸, OSO₂R⁸, OPOR⁸R⁹, OPR⁸R⁹, OPSR⁸R⁹,     NR¹⁰R¹¹, ONR¹¹R¹2, N-linked heterocyclyl or O—(N-linked     heterocyclyl), where the heterocyclyl radical of the two     last-mentioned substituents may be partially or fully halogenated     and/or may carry one to three of the following radicals:     -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or         C₁–C₄-haloalkoxy; -   R⁶ is halogen, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl,     di-(C₁–C₆-alkoxy)methyl, di-(C₁–C₆-alkylthio)methyl,     (C₁–C₆-alkoxy)(C₁–C₆-alkylthio)methyl, hydroxyl, C₁–C₆-alkoxy,     C₁–C₆-haloalkoxy, C₁–C₆-alkoxycarbonyloxy, C₁–C₆-alkylthio,     C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfonyl, C₁–C₆-haloalkylsulfonyl,     C₁–C₆-alkylcarbonyl, C₁–C₆-haloalkylcarbonyl, C₁–C₆-alkoxycarbonyl     or C₁–C₆-haloalkoxycarbonyl; -   or     -   two radicals R⁶, which are linked to the same carbon, together         form an —O—(CH₂)_(m)—O—, —O—(CH₂)_(m)—S—, —S—(CH₂)_(m)—S—,         —O—(CH₂)^(n)- or —S—(CH₂)_(n)-chain which may be substituted by         one to three radicals from the following group:         -   halogen, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl or             C₁–C₄-alkoxycarbonyl;     -   or     -   two radicals R⁶, which are linked to the same carbon, together         form a-(CH₂)_(p) chain which may be interrupted by oxygen or         sulfur and/or may be substituted by one to four radicals from         the following group:         -   halogen, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl or             C₁–C₄-alkoxycarbonyl;     -   or     -   two radicals R⁶, which are linked to the same carbon, together         with this carbon form a carbonyl group;     -   or     -   two radicals R⁶, which are linked to different carbons, together         form a-(CH₂)_(n) chain which may be substituted by one to three         radicals from the following group:         -   halogen, C₁–C₆-alkyl, C₁–C₆-alkoxy, hydroxyl or             C₁–C₆-alkoxycarbonyl; -   R⁷ is C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-haloalkenyl, C₃–C₆-alkynyl,     C₁–C₂₀-alkylcarbonyl, C₂–C₆-alkenylcarbonyl,     C₃–C₆-cycloalkylcarbonyl, C₁–C₆-alkoxycarbonyl,     C₃–C₆-alkenyloxycarbonyl, C₃–C₆-alkynyloxycarbonyl,     (C₁–C₂₀-alkylthio)carbonyl (particularly preferably     (C₁–C₆-alkylthio)carbonyl), C₁–C₆-alkylaminocarbonyl,     C₃–C₆-alkenylaminocarbonyl, C₃–C₆-alkynylaminocarbonyl,     N,N-di-(C₁–C₆-alkyl)aminocarbonyl, N—(C₃–C₆-alkenyl)-N-(C₁–C₆-alkyl)     aminocarbonyl, N—(C₃–C₆-alkynyl)-N-(C₁–C₆-alkyl)aminocarbonyl,     N—(C₁–C₆-alkoxy)-N-(C₁–C₆-alkyl)aminocarbonyl,     N—(C₃–C₆-alkenyl)-N-(C₁–C₆-alkoxy) aminocarbonyl,     N—(C₃–C₆-alkynyl)-N-(C₁–C₆-alkoxy) aminocarbonyl,     di-(C₁–C₆-alkyl)aminothiocarbonyl, C₁–C₆-alkylcarbonyl-C₁–C₆-alkyl,     C₁–C₆-alkoxyimino-C₁–C₆-alkyl, N—(C₁–C₆-alkylamino)imino-C₁–C₆-alkyl     or N,N-di-(C₁–C₆-alkylamino)imino-C₁–C₆-alkyl, where the     abovementioned alkyl, cycloalkyl and alkoxy radicals may be     partially or fully halogenated and/or may carry one to three of the     following groups:     -   cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio, C₁–C₄-alkylcarbonyl,         C₁–C₄-alkoxycarbonyl, hydroxycarbonyl,         di-(C₁–C₄-alkyl)aminocarbonyl, C₁–C₄-alkylcarbonyloxy or         C₃–C₆-cycloalkyl;     -   phenyl, heterocyclyl, phenyl-C₁–C₆-alkyl,         heterocyclyl-C₁–C₆-alkyl, phenylcarbonyl-C₁–C₆-alkyl,         heterocyclylcarbonyl-C₁–C₆-alkyl, phenylcarbonyl,         heterocyclylcarbonyl, phenoxycarbonyl, heterocyclyloxycarbonyl,         phenoxythiocarbonyl, heterocyclyloxythiocarbonyl,         phenoxy-C₁–C₆-alkylcarbonyl,         heterocyclyloxy-C₁–C₆-alkylcarbonyl,         phenyl-C₂–C₆-alkenylcarbonyl or         heterocyclyl-C₂–C₆-alkenylcarbonyl, where the phenyl and the         heterocyclyl radical of the 16 last mentioned substituents may         be partially or fully halogenated and/or may carry one to three         of the following radicals:     -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or         C₁–C₄-haloalkoxy; -   R⁸, R⁹ are C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-haloalkenyl,     C₃–C₆-cycloalkyl, hydroxy, C₁–C₆-alkoxy, di-C₁–C₆-alkylamino, or     di-(C₁–C₆-haloalkyl)amino, where the abovementioned alkyl,     cycloalkyl and alkoxy radicals may be partially or fully halogenated     and/or may carry one to three of the following groups:     -   cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio, C₁–C₄-alkylcarbonyl,         C₁–C₄-alkoxycarbonyl, hydroxycarbonyl,         di-(C₁–C₄-alkyl)aminocarbonyl, C₁–C₄-alkylcarbonyloxy or         C₃–C₆-cycloalkyl;     -   phenyl, heterocyclyl, phenyl-C₁–C₆-alkyl,         heterocyclyl-C₁–C₆-alkyl, phenoxy, heterocyclyloxy, where the         phenyl- and the heterocyclyl radical of the last-mentioned         substituents may be partially or fully halogenated and/or may         carry one to three of the following radicals:     -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or         C₁–C₄-haloalkoxy; -   R¹⁰ is C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-haloalkenyl,     C₃–C₆-cycloalkyl, C₁–C₆-alkoxy, C₃–C₆-alkenyloxy or     di-(C₁–C₆-alkyl)amino, where the abovementioned alkyl, cycloalkyl     and alkoxy radicals may be partially or fully halogenated and/or may     carry one to three radicals from the following group:     -   cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio, C₁–C₄-alkylcarbonyl,         C₁–C₄-alkoxycarbonyl, hydroxycarbonyl,         di-(C₁–C₄-alkyl)aminocarbonyl, C₁–C₄-alkylcarbonyloxy or         C₃–C₆-cycloalkyl;     -   phenyl, heterocyclyl, phenyl-C₁–C₆-alkyl or         heterocyclyl-C₁–C₆-alkyl, where the phenyl or heterocyclyl         radical of the four last-mentioned substituents may be partially         or fully halogenated and/or may carry one to three of the         following radicals:     -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or         C₁–C₄-haloalkoxy; -   R¹¹, R¹² are C₁–C₆-alkyl or C₃–C₆-alkenyl; -   l 0 to 6; -   m 2 to 4; -   n 1 to 5; -   p 2 to 5.

Particular preference is given to compounds of the formula I where the variables have the following meanings, either on their own or in combination:

-   R¹ is halogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₁–C₆-alkoxy,     C₁–C₆-alkylthio or C₁–C₆-alkylsulfonyl; in particular halogen, such     as fluorine or chlorine, C₁–C₆-alkyl, such as methyl or ethyl,     C₁–C₆-haloalkyl, such as difluoromethyl or trifluoromethyl;     particularly preferably fluorine, chlorine, methyl, difluoromethyl     or trifluoromethyl; -   R² is hydrogen or C₁–C₆-alkyl, such as methyl or ethyl; in     particular hydrogen or methyl; -   R³ is hydrogen or C₁–C₆-alkyl; in particular hydrogen; -   R⁴ is a compound IIa or IIb

where

-   R⁵ is halogen, OR⁷, SR⁷, SO₂R⁸, OSO₂R⁸, NR¹⁰R¹¹, ONR¹¹R¹², N-linked     heterocyclyl or O—(N-linked heterocyclyl), where the heterocyclyl     radical of the two last-mentioned substituents may be partially or     fully halogenated and/or may carry one to three of the following     radicals:     -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or         C₁–C₄-haloalkoxy; -   R⁶ is halogen, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl,     di-(C₁–C₆-alkoxy)methyl, di-(C₁–C₆-alkylthio)methyl,     (C₁–C₆-alkoxy)(C₁–C₆-alkylthio)methyl, hydroxyl, C₁–C₆-alkoxy,     C₁–C₆-haloalkoxy, C₁–C₆-alkoxycarbonyloxy, C₁–C₆-alkylthio or     C₁–C₆-haloalkylthio; -   or -   two radicals R⁶, which are linked to the same carbon, together with     this carbon form a carbonyl group; -   R⁷ is C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-haloalkenyl, C₃–C₆-alkynyl,     C₁–C₂₀-alkylcarbonyl, C₃–C₆-cycloalkylcarbonyl,     C₁–C₆-alkoxycarbonyl, C₃–C₆-alkenyloxycarbonyl,     C₁–C₆-alkylaminocarbonyl, C₃–C₆-alkenylaminocarbonyl,     N,N-di-(C₁–C₆-alkyl)aminocarbonyl,     N—(C₃–C₆-alkenyl)-N-(C₁-₆-alkyl)aminocarbonyl,     N—(C₁–C₆-alkoxy)-N-(C₁–C₆-alkyl) aminocarbonyl,     N—(C₃–C₆-alkenyl)-N-(C₁–C₆-alkoxy) aminocarbonyl, di-(C₁–C₆-alkyl)     aminothiocarbonyl or abovementioned alkyl, cycloalkyl and alkoxy     radicals may be partially or fully halogenated and/or may carry one     to three of the following groups: cyano, C₁–C₄-alkoxy,     C₁–C₄-alkylthio, C₁–C₄-alkylcarbonyl, C₁–C₄-alkoxycarbonyl,     hydroxycarbonyl, di-(C₁–C₄-alkyl)aminocarbonyl,     C₁–C₄-alkylcarbonyloxy or C₃–C₆-cycloalkyl;     -   phenyl, heterocyclyl, phenyl-C₁–C₆-alkyl,         heterocyclyl-C₁–C₆-alkyl, phenylcarbonyl-C₁–C₆-alkyl,         heterocyclylcarbonyl-C₁–C₆-alkyl, phenylcarbonyl,         heterocyclylcarbonyl, phenoxycarbonyl, heterocyclyloxycarbonyl,         phenoxythiocarbonyl, heterocyclyloxythiocarbonyl,         phenoxy-C₁–C₆-alkylcarbonyl or         heterocyclyloxy-C₁–C₆-alkylcarbonyl, where the phenyl and the         heterocyclyl radical of the 14 last-mentioned substituents may         be partially or fully halogenated and/or may carry one to three         of the following radicals:     -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or         C₁–C₄-haloalkoxy; -   R⁸ is C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-haloalkenyl,     C₃–C₆-cycloalkyl, hydroxyl, C₁–C₆-alkoxy, di-C₁–C₆-alkylamino or     di-(C₁–C₆-haloalkyl)amino, where the abovementioned alkyl,     cycloalkyl and alkoxy radicals may be partially or fully halogenated     and/or may carry one to three of the following groups:     -   cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio, C₁–C₄-alkylcarbonyl,         C₁–C₄-alkoxycarbonyl, hydroxycarbonyl,         di-(C₁–C₄-alkyl)aminocarbonyl, C₁–C₄-alkylcarbonyloxy or         C₃–C₆-cycloalkyl;     -   phenyl, heterocyclyl, phenyl-C₁–C₆-alkyl,         heterocyclyl-C₁–C₆-alkyl, phenoxy, heterocyclyloxy, where the         phenyl and the heterocyclyl radical of the last-mentioned         substituents may be partially or fully halogenated and/or may         carry one to three of the following radicals:     -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or         C₁–C₄-haloalkoxy; -   R¹⁰ is C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-haloalkenyl,     C₃–C₆-cycloalkyl, C₁–C₆-alkoxy, C₃–C₆-alkenyloxy or     di-(C₁–C₆-alkyl)amino, where the abovementioned alkyl, cycloalkyl     and alkoxy radicals may be partially or fully halogenated and/or may     carry one to three radicals from the following group:     -   cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio, C₁–C₄-alkylcarbonyl,         C₁–C₄-alkoxycarbonyl, hydroxycarbonyl,         di-(C₁–C₄-alkyl)aminocarbonyl, C₁–C₄-alkylcarbonyloxy or         C₃–C₆-cycloalkyl;     -   phenyl, heterocyclyl, phenyl-C₁–C₆-alkyl or         heterocyclyl-C₁–C₆-alkyl, where the phenyl or heterocyclyl         radical of the four last-mentioned substituents may be partially         or fully halogenated and/or may carry one to three of the         following radicals:     -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or         C₁–C₄-haloalkoxy; -   R¹¹, R¹² are C₁–C₆-alkyl or C₃–C₆-alkenyl; is 0 to 6.

Particular preference is also given to the compounds of the formula I where the variables have the following meaning, on their own or in combination:

-   R¹ is halogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₁–C₆-alkoxy,     C₁–C₆-alkylthio, heterocyclyloxy or phenylthio, where the two     last-mentioned radicals may be partially or fully halogenated and/or     may carry one to three of the substituents mentioned below:     -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or         C₁–C₄-haloalkoxy; particularly preferably halogen, C₁–C₆-alkyl         or C₁–C₆-alkylthio; -   R² is hydrogen, C₁–C₆-alkyl or C₁–C₆-haloalkyl; particularly     preferably hydrogen; -   R³ is hydrogen; -   R⁵ is halogen, OR⁷, SR⁷, SOR⁸, SO₂R⁸, OSO₂R⁸, OPR⁸R⁹, OPOR⁸R⁹,     OPSR⁸R⁹, NR¹⁰R¹¹ or N-bonded heterocyclyl which may be partially or     fully halogenated and/or may carry one to three of the following     radicals:     -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or         C₁–C₄-haloalkoxy;     -   particularly preferably halogen, OR⁷, NR¹⁰R¹¹ or N-bonded         heterocyclyl which may be partially or fully halogenated and/or         may carry one to three of the following radicals:     -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or         C₁–C₄-haloalkoxy;     -   particularly preferably fluorine, OR⁷, NR¹⁰R¹¹ or N-bonded         heterocyclyl selected from the group consisting of 4-morpholinyl         or 4-oxo-1,4-dihydropyrid-1-yl; -   R⁶ is C₁–C₆-alkyl or two radicals R⁶ which are attached to the same     carbon form, together with this carbon, a carbonyl group; -   R⁷ is C₁–C₆-alkyl, C₁–C₂₀-alkylcarbonyl, C₁–C₆-alkoxycarbonyl,     (C₁–C₂₀-alkylthio)carbonyl, N,N-di-(C₁–C₆-alkyl)aminocarbonyl,     phenyl, phenylcarbonyl or phenoxy-C₁–C₆-alkylcarbonyl, where the     phenyl radical of the three last-mentioned substituents may be     partially or fully halogenated and/or may carry one to three of the     following radicals:     -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or         C₁–C₄-haloalkoxy; particularly preferably C₁–C₆-alkyl,         C₁–C₂₀-alkylcarbonyl, C₁–C₆-alkoxycarbonyl,         (C₁–C₆-alkylthio)carbonyl, N,N-di-(C₁–C₆-alkyl)aminocarbonyl,         phenyl, phenylcarbonyl or phenoxy-C₁–C₆-alkylcarbonyl, where the         phenyl radical of the three last-mentioned substituents may be         partially or fully halogenated and/or may carry one to three of         the following radicals:     -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or         C₁–C₄-haloalkoxy; particularly preferably         C₁–C₂₀-alkylthiocarbonyl; most preferably         C₁–C₆-alkylthiocarbonyl; -   R⁸,R⁹ are C₁–C₆-alkyl, C₁–C₆-alkoxy, di-(C₁–C₆-alkyl)amino or     phenyl, where the last-mentioned radical may be partially or fully     halogenated and/or may carry one to three of the following radicals:     -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or         C₁–C₄-haloalkoxy; -   R¹⁰ is C₁–C₆-alkyl or C₁–C₆-alkoxy; -   R¹¹ is C₁–C₆-alkyl; -   l is from 0 to 6; particularly preferably from 4 to 6; in particular     6.

Particular preference is also given to compounds of the formula I where

-   R⁶ is nitro, halogen, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl,     di-(C₁–C₆-alkoxy)methyl, di-(C₁–C₆-alkylthio)methyl,     (C₁–c₆-alkoxy)(C₁–C₆-alkylthio)methyl, hydroxyl, C₁–C₆-alkoxy,     C₁–C₆-haloalkoxy, C₁–C₆-alkoxycarbonyloxy, C₁–C₆-alkylthio,     C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl,     C₁–C₆-alkylsulfonyl, C₁–C₆-haloalkylsulfonyl, C₁–C₆-alkylcarbonyl,     C₁–C₆-haloalkylcarbonyl, C₁–C₆-alkoxycarbonyl or     C₁–C₆-haloalkoxycarbonyl; -   or -   two radicals R⁶, which are linked to the same carbon, together form     an —O—(CH₂)_(m)—O—, —O—(CH₂)_(m)—O—, —O—(CH₂)_(m)—S—,     —S—(CH₂)_(m)—S—, —O—(CH₂)_(n)— or —S—(CH₂)_(n) chain which may be     substituted by one to three radicals from the following group:     -   halogen, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl or         C₁–C₄-alkoxycarbonyl; -   or -   two radicals R⁶, which are linked to the same carbon, form a     —(CH₂)_(p) chain which may be interrupted by oxygen or sulfur and/or     which may be substituted by one to four radicals from the following     group:     -   halogen, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl or         C₁–C₄-alkoxycarbonyl; -   or -   two radicals R⁶, which are linked to the same carbon, together with     this carbon form a carbonyl group.

Particular preference is given to compounds of the formula I here

-   R⁶ is nitro, halogen, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl,     di-(C₁–C₆-alkoxy)methyl, di-(C₁–C₆-alkylthio)methyl,     (C₁–C₆-alkoxy)(C₁–C₆-alkylthio)methyl, hydroxyl, C₁–C₆-alkoxy,     C₁–C₆-haloalkoxy, C₁–C₆-alkoxycarbonyloxy, C₁–C₆-alkylthio,     C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl,     C₁–C₆-alkylsulfonyl, C₁–C₆-haloalkylsulfonyl, C₁–C₆-alkylcarbonyl,     C₁–C₆-haloalkylcarbonyl, C₁–C₆-alkoxycarbonyl or     C₁–C₆-haloalkoxycarbonyl; -   or -   two radicals R⁶, which are linked to the same carbon, together with     this carbon form a carbonyl group.

Particular preference is also given to the compounds of the formula I where

-   R⁵ is halogen or (C₁–C₂₀-alkylthio)carbonyloxy; particularly     preferably fluorine or (C₁–C₆-alkylthio)carbonyloxy;

Particular preference is also given to the compounds of the formula I where

-   R⁵ is NR¹⁰R¹¹ or N-linked heterocyclyl which may be partially or     fully halogenated and/or may carry one to three of the following     radicals:     -   nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or         C₁–C₄-haloalkoxy;

Particular preference is also given to the compounds of the formula I where R⁴ has the following meanings:

Very particular preference is given to the compounds of the formula I where

-   R⁵ is NR¹⁰R¹¹ or tetrahydropyrrol-1-yl, 2,3-dihydro-1H-pyrrol-1-yl,     2,5-dihydro-1H-pyrrol-1-yl, pyrrol-1-yl, tetrahydropyrazol-1-yl,     tetrahydroisoxazol-2-yl, tetrahydrothiazol-2-yl,     tetrahydroimidazol-1-yl, tetrahydrooxazol-3-yl,     tetrahydrothiazol-3-yl, pyrazol-1-yl, imidazol-1-yl,     1,2,4-triazol-1-yl, tetrazol-1-yl, piperidin-1-yl,     4-oxo-1,4-dihydro-1-pyridyl, hexahydropyrimidin-1-yl,     hexahydropyrazin-1-yl, tetrahydro-1,4-oxazin-4-yl,     tetrahydro-1,2-oxazin-2-yl, succinimide, maleimide or glutarimide,     where the abovementioned heterocycles may be partially or fully     halogenated and/or may carry one to three of the following radicals:     -   nitro, cyano, C₁–C₄-alkyl, such as methyl or ethyl,         C₁–C₄-haloalkyl such as chloromethyl, difluoromethyl or         trifluoromethyl, C₁–C₄-alkoxy, such as methoxy or ethoxy or         C₁–C₄-haloalkoxy such as difluoromethoxy or trifluoromethoxy; -   R¹⁰ C₁–C₆-alkoxy

Extraordinary preference is given to compounds of the formula Ia1 and Ib1 (≡I where l=0), in particular to the compounds Ia1.1 to Ia1.456 and the compounds Ib1.1 to Ib1.456, where the radical definitions R¹ to R⁵ and 1 have a preferred meaning for the compounds according to the invention not only in combination with each other, but in each case also on their own.

TABLE 1 Ia1

Ib1

No. R¹ R² R³ R⁵ Ia1.1 or Ib1.1 CH₃ H H F Ia1.2 or Ib1.2 CH₃ H H Cl Ia1.3 or Ib1.3 CH₃ H H Br Ia1.4 or Ib1.4 CH₃ H H I Ia1.5 or Ib1.5 CH₃ H H SCH₃ Ia1.6 or Ib1.6 CH₃ H H SCH₂CH₃ Ia1.7 or Ib1.7 CH₃ H H SCO(N(CH₃)₂)₂ Ia1.8 or Ib1.8 CH₃ H H SO₂CH₃ Ia1.9 or Ib1.9 CH₃ H H SO₂CH₂CH₃ Ia1.10 or Ib1.10 CH₃ H H SC₆H₅ Ia1.11 or Ib1.11 CH₃ H H S(4-CH₃—C₆H₄) Ia1.12 or Ib1.12 CH₃ H H S(4-Cl—C₆H₄) Ia1.13 or Ib1.13 CH₃ H H SO₂C₆H₅ Ia1.14 or Ib1.14 CH₃ H H SO₂(4-CH₃—C₆H₄) Ia1.15 or Ib1.15 CH₃ H H SO₂(4-Cl—C₆H₄) Ia1.16 or Ib1.16 CH₃ H H 4-morpholinyl Ia1.17 or Ib1.17 CH₃ H H 1-pyrrolidinyl Ia1.18 or Ib1.18 CH₃ H H 1-(1,2,4-triazolyl) Ia1.19 or Ib1.19 CH₃ H H 1-imidazolyl Ia1.20 or Ib1.20 CH₃ H H 1-pyrazolyl Ia1.21 or Ib1.21 CH₃ H H 4-oxo-1,4-dihydro-1- pyridyl Ia1.22 or Ib1.22 CH₃ H H N(OCH₃)CH₃ Ia1.23 or Ib1.23 CH₃ H H 2-tetrahydroisoxazolyl Ia1.24 or Ib1.24 CH₃ H H N(CH₃)N(CH₃)₂ Ia1.25 or Ib1.25 CH₃ H H N(CH₂CH═CH₂)N(CH₃)₂ Ia1.26 or Ib1.26 CH₃ H H OPO(OCH₃)₂ Ia1.27 or Ib1.27 CH₃ H H OPO(OCH₂CH₃)₂ Ia1.28 or Ib1.28 CH₃ H H OPO(N(CH₃)₂)₂ Ia1.29 or Ib1.29 CH₃ H H OPO(OC₆H₅)₂ Ia1.30 or Ib1.30 CH₃ H H OPO(CH₃)₂ Ia1.31 or Ib1.31 CH₃ H H OPO(CH₂CH₃)₂ Ia1.32 or Ib1.32 CH₃ H H OPO(C₆H₅)₂ Ia1.33 or Ib1.33 CH₃ H H OPS(OCH₃)₂ Ia1.34 or Ib1.34 CH₃ H H OPS(OCH₂CH₃)₂ Ia1.35 or Ib1.35 CH₃ H H OP(OCH₃)₂ Ia1.36 or Ib1.36 CH₃ H H OP(OCH₂CH₃)₂ Ia1.37 or Ib1.37 CH₃ H H PO(OCH₃)₂ Ia1.38 or Ib1.38 CH₃ H H PO(OCH₂CH₃)₂ Ia1.39 or Ib1.39 CH₃ H H PO(C₆H₅)₂ Ia1.40 or Ib1.40 CH₃ H H OCH₃ Ia1.41 or Ib1.41 CH₃ H H OCH₂CH₃ Ia1.42 or Ib1.42 CH₃ H H OCH₂C₆H₅ Ia1.43 or Ib1.43 CH₃ H H OCH₂(2-furyl) Ia1.44 or Ib1.44 CH₃ H H OCH₂(3-furyl) Ia1.45 or Ib1.45 CH₃ H H OCOOCH₃ Ia1.46 or Ib1.46 CH₃ H H OCOOCH₂CH₃ Ia1.47 or Ib1.47 CH₃ H H OCOOCH(CH₃)₂ Ia1.48 or Ib1.48 CH₃ H H OCOOC₆H₅ Ia1.49 or Ib1.49 CH₃ H H OCOOC(CH₃)₃ Ia1.50 or Ib1.50 CH₃ H H OCSOC₆H₅ Ia1.51 or Ib1.51 CH₃ H H OCSN(CH₃)₂ Ia1.52 or Ib1.52 CH₃ H H OCON(CH₃)₂ Ia1.53 or Ib1.53 CH₃ H H OCOSCH₃ Ia1.54 or Ib1.54 CH₃ H H ON(CH₃)₂ Ia1.55 or Ib1.55 CH₃ H H O-1-piperidyl Ia1.56 or Ib1.56 CH₃ H H OCOCH₃ Ia1.57 or Ib1.57 CH₃ H H OCOCH₂CH₃ Ia1.58 or Ib1.58 CH₃ H H OCOCH(CH₃)₂ Ia1.59 or Ib1.59 CH₃ H H OCOC(CH₃ ₎₃ Ia1.60 or Ib1.60 CH₃ H H OCO(CH₂)₆CH₃ Ia1.61 or Ib1.61 CH₃ H H OCO(CH₂)₇CH₃ Ia1.62 or Ib1.62 CH₃ H H OCO(CH₂)₁₆CH₃ Ia1.63 or Ib1.63 CH₃ H H OCO(CH₂)₁₄CH₃ Ia1.64 or Ib1.64 CH₃ H H OCOCH₂CH₂CH═CH₂ Ia1.65 or Ib1.65 CH₃ H H OCO(CH₂)₃O(2,4-Cl₂—C₆H₃) Ia1.66 or Ib1.66 CH₃ H H OCOCH(CH₃)O— (2-CH₃-4-Cl—C₆H₃) Ia1.67 or Ib1.67 CH₃ H H OCOcyclopropyl Ia1.68 or Ib1.68 CH₃ H H OCOcyclopentyl Ia1.69 or Ib1.69 CH₃ H H OCOcyclohexyl Ia1.70 or Ib1.70 CH₃ H H OCOC₆H₅ Ia1.71 or Ib1.71 CH₃ H H OCO(2-tetrahydrofuryl) Ia1.72 or Ib1.72 CH₃ H H OCO(2-furyl) Ia1.73 or Ib1.73 CH₃ H H OCO(2-thienyl) Ia1.74 or Ib1.74 CH₃ H H OCO(3-pyridyl) Ia1.75 or Ib1.75 CH₃ H H OSO₂CH₃ Ia1.76 or Ib1.76 CH₃ H H OSO₂CH₂CH₃ Ia1.77 or Ib1.77 F H H F Ia1.78 or Ib1.78 F H H Cl Ia1.79 or Ib1.79 F H H Br Ia1.80 or Ib1.80 F H H I Ia1.81 or Ib1.81 F H H SCH₃ Ia1.82 or Ib1.82 F H H SCH₂CH₃ Ia1.83 or Ib1.83 F H H SCO(N(CH₃)₂)₂ Ia1.84 or Ib1.84 F H H SO₂CH₃ Ia1.85 or Ib1.85 F H H SO₂CH₂CH₃ Ia1.86 or Ib1.86 F H H SC₆H₅ Ia1.87 or Ib1.87 F H H S(4-CH₃—C₆H₄) Ia1.88 or Ib1.88 F H H S(4-Cl—C₆H₄) Ia1.89 or Ib1.89 F H H SO₂C₆H₅ Ia1.90 or Ib1.90 F H H SO₂(4-CH₃—C₆H₄) Ia1.91 or Ib1.91 F H H SO₂(4-Cl—C₆H₄) Ia1.92 or Ib1.92 F H H 4-morpholinyl Ia1.93 or Ib1.93 F H H 1-pyrrolidinyl Ia1.94 or Ib1.94 F H H 1-(1,2,4-triazolyl) Ia1.95 or Ib1.95 F H H 1-imidazolyl Ia1.96 or Ib1.96 F H H 1-pyrazolyl Ia1.97 or Ib1.97 F H H 4-oxo-1,4-dihydro-1- pyridyl Ia1.98 or Ib1.98 F H H N(OCH₃)CH₃ Ia1.99 or Ib1.99 F H H 2-tetrahydroisoxazolyl Ia1.100 or Ib1.100 F H H N(CH₃)N(CH₃)₂ Ia1.101 or Ib1.101 F H H N(CH₂CH═CH₂)N(CH₃)₂ Ia1.102 or Ib1.102 F H H OPO(OCH₃)₂ Ia1.103 or Ib1.103 F H H OPO(N(CH₃)₂)₂ Ia1.104 or Ib1.104 F H H OPO(OCH₂CH₃)₂ Ia1.105 or Ib1.105 F H H OPO(OC₆H₅)₂ Ia1.106 or Ib1.106 F H H OPO(CH₃)₂ Ia1.107 or Ib1.107 F H H OPO(CH₂CH₃)₂ Ia1.108 or Ib1.108 F H H OPO(C₆H₅)₂ Ia1.109 or Ib1.109 F H H OPS(OCH₃)₂ Ia1.110 or Ib1.110 F H H OPS(OCH₂CH₃)₂ Ia1.111 or Ib1.111 F H H OP(OCH₃)₂ Ia1.112 or Ib1.112 F H H OP(OCH₂CH₃)₂ Ia1.113 or Ib1.113 F H H PO(OCH₃)₂ Ia1.114 or Ib1.114 F H H PO(OCH₂CH₃)₂ Ia1.115 or Ib1.115 F H H PO(C₆H₅)₂ Ia1.116 or Ib1.116 F H H OCH₃ Ia1.117 or Ib1.117 F H H OCH₂CH₃ Ia1.118 or Ib1.118 F H H OCH₂C₆H₅ Ia1.119 or Ib1.119 F H H OCH₂(2-furyl) Ia1.120 or Ib1.120 F H H OCH₂(3-furyl) Ia1.121 or Ib1.121 F H H OCOOCH₃ Ia1.122 or Ib1.122 F H H OCOOCH₂CH₃ Ia1.123 or Ib1.123 F H H OCOOCH(CH₃)₂ Ia1.124 or Ib1.124 F H H OCOOC₆H₅ Ia1.125 or Ib1.125 F H H OCOOC(CH₃)₃ Ia1.126 or Ib1.126 F H H OCSOC₆H₅ Ia1.127 or Ib1.127 F H H OCSN(CH₃)₂ Ia1.128 or Ib1.128 F H H OCON(CH₃)₂ Ia1.129 or Ib1.129 F H H OCOSCH₃ Ia1.130 or Ib1.130 F H H ON(CH₃)₂ Ia1.131 or Ib1.131 F H H O-1-piperidyl Ia1.132 or Ib1.132 F H H OCOCH₃ Ia1.133 or Ib1.133 F H H OCOCH₂CH₃ Ia1.134 or Ib1.134 F H H OCOCH(CH₃)₂ Ia1.135 or Ib1.135 F H H OCOC(CH₃)₃ Ia1.136 or Ib1.136 F H H OCO(CH₂)₆CH₃ Ia1.137 or Ib1.137 F H H OCO(CH₂)₇CH₃ Ia1.138 or Ib1.138 F H H OCO(CH₂)₁₆CH₃ Ia1.139 or Ib1.139 F H H OCO(CH₂)₁₄CH₃ Ia1.140 or Ib1.140 F H H OCOCH₂CH₂CH═CH₂ Ia1.141 or Ib1.141 F H H OCO(CH₂)₃O(2,4-Cl₂—C₆H₃) Ia1.142 or Ib1.142 F H H OCOCH(CH₃)O— (2-CH₃-4-Cl—C₆H₃) Ia1.143 or Ib1.143 F H H OCOcyclopropyl Ia1.144 or Ib1.144 F H H OCOcyclopentyl Ia1.145 or Ib1.145 F H H OCOcyclohexyl Ia1.146 or Ib1.146 F H H OCOC₆H₅ Ia1.147 or Ib1.147 F H H OCO(2-tetrahydrofuryl) Ia1.148 or Ib1.148 F H H OCO(2-furyl) Ia1.149 or Ib1.149 F H H OCO(2-thienyl) Ia1.150 or Ib1.150 F H H OCO(3-pyridyl) Ia1.151 or Ib1.151 F H H OSO₂CH₃ Ia1.152 or Ib1.152 F H H OSO₂CH₂CH₃ Ia1.153 or Ib1.153 CF₃ H H F Ia1.154 or Ib1.154 CF₃ H H Cl Ia1.155 or Ib1.155 CF₃ H H Br Ia1.156 or Ib1.156 CF₃ H H I Ia1.157 or Ib1.157 CF₃ H H SCH₃ Ia1.158 or Ib1.158 CF₃ H H SCH₂CH₃ Ia1.159 or Ib1.159 CF₃ H H SCO(N(CH₃)₂)₂ Ia1.160 or Ib1.160 CF₃ H H SO₂CH₃ Ia1.161 or Ib1.161 CF₃ H H SO₂CH₂CH₃ Ia1.162 or Ib1.162 CF₃ H H SC₆H₅ Ia1.163 or Ib1.163 CF₃ H H S(4-CH₃—C₆H₄) Ia1.164 or Ib1.164 CF₃ H H S(4-Cl—C₆H₄) Ia1.165 or Ib1.165 CF₃ H H SO₂C₆H₅ Ia1.166 or Ib1.166 CF₃ H H SO₂(4-CH₃—C₆H₄) Ia1.167 or Ib1.167 CF₃ H H SO₂(4-Cl—C₆H₄) Ia1.168 or Ib1.168 CF₃ H H 4-morpholinyl Ia1.169 or Ib1.169 CF₃ H H 1-pyrrolidinyl Ia1.170 or Ib1.170 CF₃ H H 1-(1,2,4-triazolyl) Ia1.171 or Ib1.171 CF₃ H H 1-imidazolyl Ia1.172 or Ib1.172 CF₃ H H 1-pyrazolyl Ia1.173 or Ib1.173 CF₃ H H 4-oxo-1,4-dihydro-1- pyridyl Ia1.174 or Ib1.174 CF₃ H H N(OCH₃)CH₃ Ia1.175 or Ib1.175 CF₃ H H 2-tetrahydroisoxazolyl Ia1.176 or Ib1.176 CF₃ H H N(CH₃)N(CH₃)₂ Ia1.177 or Ib1.177 CF₃ H H N(CH₂CHCH₂)N(CH₃)₂ Ia1.178 or Ib1.178 CF₃ H H OPO(OCH₃)₂ Ia1.179 or Ib1.179 CF₃ H H OPO(OCH₂CH₃)₂ Ia1.180 or Ib1.180 CF₃ H H OPO(N(CH₃)₂)₂ Ia1.181 or Ib1.181 CF₃ H H OPO(OC₆H₅)₂ Ia1.182 or Ib1.182 CF₃ H H OPO(CH₃)₂ Ia1.183 or Ib1.183 CF₃ H H OPO(CH₂CH₃)₂ Ia1.184 or Ib1.184 CF₃ H H OPO(C₆H₅)₂ Ia1.185 or Ib1.185 CF₃ H H OPS(OCH₃)₂ Ia1.186 or Ib1.186 CF₃ H H OPS(OCH₂CH₃)₂ Ia1.187 or Ib1.187 CF₃ H H OP(OCH₃)₂ Ia1.188 or Ib1.188 CF₃ H H OP(OCH₂CH₃)₂ Ia1.189 or Ib1.189 CF₃ H H PO(OCH₃)₂ Ia1.190 or Ib1.190 CF₃ H H PO(OCH₂CH₃)₂ Ia1.191 or Ib1.191 CF₃ H H PO(C₆H₅)₂ Ia1.192 or Ib1.192 CF₃ H H OCH₃ Ia1.193 or Ib1.193 CF₃ H H OCH₂CH₃ Ia1.194 or Ib1.194 CF₃ H H OCH₂C₆H₅ Ia1.195 or Ib1.195 CF₃ H H OCH₂(2-furyl) Ia1.196 or Ib1.196 CF₃ H H OCH₂(3-furyl) Ia1.197 or Ib1.197 CF₃ H H OCOOCH₃ Ia1.198 or Ib1.198 CF₃ H H OCOOCH₂CH₃ Ia1.199 or Ib1.199 CF₃ H H OCOOCH(CH₃)₂ Ia1.200 or Ib1.200 CF₃ H H OCOOC₆H₅ Ia1.201 or Ib1.201 CF₃ H H OCOOC(CH₃)₃ Ia1.202 or Ib1.202 CF₃ H H OCSOC₆H₅ Ia1.203 or Ib1.203 CF₃ H H OCSN(CH₃)₂ Ia1.204 or Ib1.204 CF₃ H H OCON(CH₃)₂ Ia1.205 or Ib1.205 CF₃ H H OCOSCH₃ Ia1.206 or Ib1.206 CF₃ H H ON(CH₃)₂ Ia1.207 or Ib1.207 CF₃ H H O-1-piperidyl Ia1.208 or Ib1.208 CF₃ H H OCOCH₃ Ia1.209 or Ib1.209 CF₃ H H OCOCH₂CH₃ Ia1.210 or Ib1.210 CF₃ H H OCOCHC(CH₃)₂ Ia1.211 or Ib1.211 CF₃ H H OCOC(CH₃)₃ Ia1.212 or Ib1.212 CF₃ H H OCO(CH₂)₆CH₃ Ia1.213 or Ib1.213 CF₃ H H OCO(CH₂)₇CH₃ Ia1.214 or Ib1.214 CF₃ H H OCO(CH₂)₁₆CH₃ Ia1.215 or Ib1.215 CF₃ H H OCO(CH₂)₁₄CH₃ Ia1.216 or Ib1.216 CF₃ H H OCOCH₂CH₂CH═CH₂ Ia1.217 or Ib1.217 CF₃ H H OCO(CH₂)₃O(2,4-Cl₂—C₆H₃) Ia1.218 or Ib1.218 CF₃ H H OCOCH(CH₃)O— (2-CH₃-4-Cl—C₆H₃) Ia1.219 or Ib1.219 CF₃ H H OCOcyclopropyl Ia1.220 or Ib1.220 CF₃ H H OCOcyclopentyl Ia1.221 or Ib1.221 CF₃ H H OCOcyclohexyl Ia1.222 or Ib1.222 CF₃ H H OCOC₆H₅ Ia1.223 or Ib1.223 CF₃ H H OCO(2-tetrahydrofuryl) Ia1.224 or Ib1.224 CF₃ H H OCO(2-furyl) Ia1.225 or Ib1.225 CF₃ H H OCO(2-thienyl) Ia1.226 or Ib1.226 CF₃ H H OCO(3-pyridyl) Ia1.227 or Ib1.227 CF₃ H H OSO₂CH₃ Ia1.228 or Ib1.228 CF₃ H H OSO₂CH₂CH₃ Ia1.229 or Ib1.229 Cl H H F Ia1.230 or Ib1.230 Cl H H Cl Ia1.231 or Ib1.231 Cl H H Br Ia1.232 or Ib1.232 Cl H H I Ia1.233 or Ib1.233 Cl H H SCH₃ Ia1.234 or Ib1.234 Cl H H SCH₂CH₃ Ia1.235 or Ib1.235 Cl H H SCO(N(CH₃)₂)₂ Ia1.236 or Ib1.236 Cl H H SO₂CH₃ Ia1.237 or Ib1.237 Cl H H SO₂CH₂CH₃ Ia1.238 or Ib1.238 Cl H H SC₆H₅ Ia1.239 or Ib1.239 Cl H H S(4-CH₃—C₆H₄) Ia1.240 or Ib1.240 Cl H H S(4-Cl—C₆H₄) Ia1.241 or Ib1.241 Cl H H SO₂C₆H₅ Ia1.242 or Ib1.242 Cl H H SO₂(4-CH₃—C₆H₄) Ia1.243 or Ib1.243 Cl H H SO₂(4-Cl—C₆H₄) Ia1.244 or Ib1.244 Cl H H 4-morpholinyl Ia1.245 or Ib1.245 Cl H H 1-pyrrolidinyl Ia1.246 or Ib1.246 Cl H H 1-(1,2,4-triazolyl) Ia1.247 or Ib1.247 Cl H H 1-imidazolyl Ia1.248 or Ib1.248 Cl H H 1-pyrazolyl Ia1.249 or Ib1.249 Cl H H 4-oxo-1,4-dihydro-1- pyridyl Ia1.250 or Ib1.250 Cl H H N(OCH₃)CH₃ Ia1.251 or Ib1.251 Cl H H 2-tetrahydroisoxazolyl Ia1.252 or Ib1.252 Cl H H N(CH₃)N(CH₃)₂ Ia1.253 or Ib1.253 Cl H H N(CH₂CH═CH₂)N(CH₃)₂ Ia1.254 or Ib1.254 Cl H H OPO(OCH₃)₂ Ia1.255 or Ib1.255 Cl H H OPO(OCH₂CH₃)₂ Ia1.256 or Ib1.256 Cl H H OPO(N(CH₃)₂)₂ Ia1.257 or Ib1.257 Cl H H OPO(OC₆H₅)₂ Ia1.258 or Ib1.258 Cl H H OPO(CH₃)₂ Ia1.259 or Ib1.259 Cl H H OPO(CH₂CH₃)₂ Ia1.260 or Ib1.260 Cl H H OPO(C₆H₅)₂ Ia1.261 or Ib1.261 Cl H H OPS(OCH₃)₂ Ia1.262 or Ib1.262 Cl H H OPS(OCH₂CH₃)₂ Ia1.263 or Ib1.263 Cl H H OP(OCH₃)₂ Ia1.264 or Ib1.264 Cl H H OP(OCH₂CH₃)₂ Ia1.265 or Ib1.265 Cl H H PO(OCH₃)₂ Ia1.266 or Ib1.266 Cl H H PO(OCH₂CH₃)₂ Ia1.267 or Ib1.267 Cl H H PO(C₆H₅)₂ Ia1.268 or Ib1.268 Cl H H OCH₃ Ia1.269 or Ib1.269 Cl H H OCH₂CH₃ Ia1.270 or Ib1.270 Cl H H OCH₂C₆H₅ Ia1.271 or Ib1.271 Cl H H OCH₂(2-furyl) Ia1.272 or Ib1.272 Cl H H OCH₂(3-furyl) Ia1.273 or Ib1.273 Cl H H OCOOCH₃ Ia1.274 or Ib1.274 Cl H H OCOOCH₂CH₃ Ia1.275 or Ib1.275 Cl H H OCOOCH(CH₃)₂ Ia1.276 or Ib1.276 Cl H H OCOOC₆H₅ Ia1.277 or Ib1.277 Cl H H OCOOC(CH₃)₃ Ia1.278 or Ib1.278 Cl H H OCSOC₆H₅ Ia1.279 or Ib1.279 Cl H H OCSN(CH₃)₂ Ia1.280 or Ib1.280 Cl H H OCON(CH₃)₂ Ia1.281 or Ib1.281 Cl H H OCOSCH₃ Ia1.282 or Ib1.282 Cl H H ON(CH₃)₂ Ia1.283 or Ib1.283 Cl H H O-1-piperidyl Ia1.284 or Ib1.284 Cl H H OCOCH₃ Ia1.285 or Ib1.285 Cl H H OCOCH₂CH₃ Ia1.286 or Ib1.286 Cl H H OCOCH(CH₃)₂ Ia1.287 or Ib1.287 Cl H H OCOC(CH₃)₃ Ia1.288 or Ib1.288 Cl H H OCO(CH₂)₆CH₃ Ia1.289 or Ib1.289 Cl H H OCO(CH₂)₇CH₃ Ia1.290 or Ib1.290 Cl H H OCO(CH₂)₁₆CH₃ Ia1.291 or Ib1.291 Cl H H OCO(CH₂)₁₄CH₃ Ia1.292 or Ib1.292 Cl H H OCOCH₂CH₂CH═CH₂ Ia1.293 or Ib1.293 Cl H H OCO(CH₂)₃O(2,4-Cl₂—C₆H₃) Ia1.294 or Ib1.294 Cl H H OCOCH(CH₃)O— (2-CH₃-4-Cl—C₆H₃) Ia1.295 or Ib1.295 Cl H H OCOcyclopropyl Ia1.296 or Ib1.296 Cl H H OCOcyclopentyl Ia1.297 or Ib1.297 Cl H H OCOcyclohexyl Ia1.298 or Ib1.298 Cl H H OCOC₆H₅ Ia1.299 or Ib1.299 Cl H H OCO(2-tetrahydrofuryl) Ia1.300 or Ib1.300 Cl H H OCO(2-furyl) Ia1.301 or Ib1.301 Cl H H OCO(2-thienyl) Ia1.302 or Ib1.302 Cl H H OCO(3-pyridyl) Ia1.303 or Ib1.303 Cl H H OSO₂CH₃ Ia1.304 or Ib1.304 Cl H H OSO₂CH₂CH₃ Ia1.305 or Ib1.305 CHF₂ H H F Ia1.306 or Ib1.306 CHF₂ H H Cl Ia1.307 or Ib1.307 CHF₂ H H Br Ia1.308 or Ib1.308 CHF₂ H H I Ia1.309 or Ib1.309 CHF₂ H H SCH₃ Ia1.310 or Ib1.310 CHF₂ H H SCH₂CH₃ Ia1.311 or Ib1.311 CHF₂ H H SCO(N(CH₃)₂)₂ Ia1.312 or Ib1.312 CHF₂ H H SO₂CH₃ Ia1.313 or Ib1.313 CHF₂ H H SO₂CH₂CH₃ Ia1.314 or Ib1.314 CHF₂ H H SC₆H₅ Ia1.315 or Ib1.315 CHF₂ H H S(4-CH₃—C₆H₄) Ia1.316 or Ib1.316 CHF₂ H H S(4-Cl—C₆H₄) Ia1.317 or Ib1.317 CHF₂ H H SO₂C₆H₅ Ia1.318 or Ib1.318 CHF₂ H H SO₂(4-CH₃—C₆H₄) Ia1.319 or Ib1.319 CHF₂ H H SO₂(4-Cl—C₆H₄) Ia1.320 or Ib1.320 CHF₂ H H 4-morpholinyl Ia1.321 or Ib1.321 CHF₂ H H 1-pyrrolidinyl Ia1.322 or Ib1.322 CHF₂ H H 1-(1,2,4-triazolyl) Ia1.323 or Ib1.323 CHF₂ H H 1-imidazolyl Ia1.324 or Ib1.324 CHF₂ H H 1-pyrazolyl Ia1.325 or Ib1.325 CHF₂ H H 4-oxo-1,4-dihydro-1- pyridyl Ia1.326 or Ib1.326 CHF₂ H H N(OCH₃)CH₃ Ia1.327 or Ib1.327 CHF₂ H H 2-tetrahydroisoxazolyl Ia1.328 or Ib1.328 CHF₂ H H N(CH₃)N(CH₃)₃ Ia1.329 or Ib1.329 CHF₂ H H N(CH₂CH═CH₂)N(CH₃)₂ Ia1.330 or Ib1.330 CHF₂ H H OPO(OCH₃)₂ Ia1.331 or Ib1.331 CHF₂ H H OPO(OCH₂CH₃)₂ Ia1.332 or Ib1.332 CHF₂ H H OPO(N(CH₃)₂)₂ Ia1.333 or Ib1.333 CHF₂ H H OPO(OC₆H₅)₂ Ia1.334 or Ib1.334 CHF₂ H H OPO(CH₃)₂ Ia1.335 or Ib1.335 CHF₂ H H OPO(CH₂CH₃)₂ Ia1.336 or Ib1.336 CHF₂ H H OPO(C₆H₅)₂ Ia1.337 or Ib1.337 CHF₂ H H OPS(OCH₃)₂ Ia1.338 or Ib1.338 CHF₂ H H OPS(OCH₂CH₃)₂ Ia1.339 or Ib1.339 CHF₂ H H OP(OCH₃)₂ Ia1.340 or Ib1.340 CHF₂ H H OP(OCH₂CH₃)₂ Ia1.341 or Ib1.341 CHF₂ H H PO(OCH₃)₂ Ia1.342 or Ib1.342 CHF₂ H H PO(OCH₂CH₃)₂ Ia1.343 or Ib1.343 CHF₂ H H PO(C₆H₅)₂ Ia1.344 or Ib1.344 CHF₂ H H OCH₃ Ia1.345 or Ib1.345 CHF₂ H H OCH₂CH₃ Ia1.346 or Ib1.346 CHF₂ H H OCH₂C₆H₅ Ia1.347 or Ib1.347 CHF₂ H H OCH₂(2-furyl) Ia1.348 or Ib1.348 CHF₂ H H OCH₂(3-furyl) Ia1.349 or Ib1.349 CHF₂ H H OCOOCH₃ Ia1.350 or Ib1.350 CHF₂ H H OCOOCH₂CH₃ Ia1.351 or Ib1.351 CHF₂ H H OCOOCH(CH₃)₂ Ia1.352 or Ib1.352 CHF₂ H H OCOOC₆H₅ Ia1.353 or Ib1.353 CHF₂ H H OCOOC(CH₃)₃ Ia1.354 or Ib1.354 CHF₂ H H OCSOC₆H₅ Ia1.355 or Ib1.355 CHF₂ H H OCSN(CH₃)₂ Ia1.356 or Ib1.356 CHF₂ H H OCON(CH₃)₂ Ia1.357 or Ib1.357 CHF₂ H H OCOSCH₃ Ia1.358 or Ib1.358 CHF₂ H H ON(CH₃)₂ Ia1.359 or Ib1.359 CHF₂ H H O-1-piperidyl Ia1.360 or Ib1.360 CHF₂ H H OCOCH₃ Ia1.361 or Ib1.361 CHF₂ H H OCOCH₂CH₃ Ia1.362 or Ib1.362 CHF₂ H H OCOCH(CH₃)₂ Ia1.363 or Ib1.363 CHF₂ H H OCOC(CH₃)₃ Ia1.364 or Ib1.364 CHF₂ H H OCO(CH₂)₆CH₃ Ia1.365 or Ib1.365 CHF₂ H H OCO(CH₂)₇CH₃ Ia1.366 or Ib1.366 CHF₂ H H OCO(CH₂)₁₆CH₃ Ia1.367 or Ib1.367 CHF₂ H H OCO(CH₂)₁₄CH₃ Ia1.368 or Ib1.368 CHF₂ H H OCOCH₂CH₂CH═CH₂ Ia1.369 or Ib1.369 CHF₂ H H OCO(CH₂)₃O(2,4-Cl₂—C₆H₃) Ia1.370 or Ib1.370 CHF₂ H H OCOCH(CH₃)O— (2-CH₃-4-Cl—C₆H₃) Ia1.371 or Ib1.371 CHF₂ H H OCOcyclopropyl Ia1.372 or Ib1.372 CHF₂ H H OCOcyclopentyl Ia1.373 or Ib1.373 CHF₂ H H OCOcyclohexyl Ia1.374 or Ib1.374 CHF₂ H H OCOC₆H₅ Ia1.375 or Ib1.375 CHF₂ H H OCO(2-tetrahydrofuryl) Ia1.376 or Ib1.376 CHF₂ H H OCO(2-furyl) Ia1.377 or Ib1.377 CHF₂ H H OCO(2-thienyl) Ia1.378 or Ib1.378 CHF₂ H H OCO(3-pyridyl) Ia1.379 or Ib1.379 CHF₂ H H OSO₂CH₅ Ia1.380 or Ib1.380 CHF₂ H H OSO₂CH₂CH₃ Ia1.381 or Ib1.381 Cl CH₃ H F Ia1.382 or Ib1.382 Cl CH₃ H Cl Ia1.383 or Ib1.383 Cl CH₃ H Br Ia1.384 or Ib1.384 Cl CH₃ H I Ia1.385 or Ib1.385 Cl CH₃ H SCH₃ Ia1.386 or Ib1.386 Cl CH₃ H SCH₂CH₃ Ia1.387 or Ib1.387 Cl CH₃ H SCO(N(CH₃)₂)₂ Ia1.388 or Ib1.388 Cl CH₃ H SO₂CH₃ Ia1.389 or Ib1.389 Cl CH₃ H SO₂CH₂CH₃ Ia1.390 or Ib1.390 Cl CH₃ H SC₆H₅ Ia1.391 or Ib1.391 Cl CH₃ H S(4-CH₃—C₆H₄) Ia1.392 or Ib1.392 Cl CH₃ H S(4-Cl—C₆H₄) Ia1.393 or Ib1.393 Cl CH₃ H SO₂C₆H₅ Ia1.394 or Ib1.394 Cl CH₃ H SO₂(4-CH₃—C₆H₄) Ia1.395 or Ib1.395 Cl CH₃ H SO₂(4-Cl—C₆H₄) Ia1.396 or Ib1.396 Cl CH₃ H 4-morpholinyl Ia1.397 or Ib1.397 Cl CH₃ H 1-pyrrolidinyl Ia1.398 or Ib1.398 Cl CH₃ H 1-(1,2,4-triazolyl) Ia1.399 or Ib1.399 Cl CH₃ H 1-imidazolyl Ia1.400 or Ib1.400 Cl CH₃ H 1-pyrazolyl Ia1.401 or Ib1.401 Cl CH₃ H 4-oxo-1,4-dihydro-1- pyridyl Ia1.402 or Ib1.402 Cl CH₃ H N(OCH₃)CH₃ Ia1.403 or Ib1.403 Cl CH₃ H 2-tetrahydroisoxazolyl Ia1.404 or Ib1.404 Cl CH₃ H N(CH₃)N(CH₃)₂ Ia1.405 or Ib1.405 Cl CH₃ H N(CH₂CH═CH₂)N(CH₃)₂ Ia1.406 or Ib1.406 Cl CH₃ H OPO(OCH₃)₂ Ia1.407 or Ib1.407 Cl CH₃ H OPO(OCH₂CH₃)₂ Ia1.408 or Ib1.408 Cl CH₃ H OPO(N(CH₃)₂)₂ Ia1.409 or Ib1.409 Cl CH₃ H OPO(OC₆H₅)₂ Ia1.410 or Ib1.410 Cl CH₃ H OPO(CH₃)₂ Ia1.411 or Ib1.411 Cl CH₃ H OPO(CH₂CH₃)₂ Ia1.412 or Ib1.412 Cl CH₃ H OPO(C₆H₅)₂ Ia1.413 or Ib1.413 Cl CH₃ H OPS(OCH₃)₂ Ia1.414 or Ib1.414 Cl CH₃ H OPS(OCH₂CH₃)₂ Ia1.415 or Ib1.415 Cl CH₃ H OP(OCH₃)₂ Ia1.416 or Ib1.416 Cl CH₃ H OP(OCH₂CH₃)₂ Ia1.417 or Ib1.417 Cl CH₃ H PO(OCH₃)₂ Ia1.418 or Ib1.418 Cl CH₃ H PO(OCH₂CH₃)₂ Ia1.419 or Ib1.419 Cl CH₃ H PO(C₆H₅)₂ Ia1.420 or Ib1.420 Cl CH₃ H OCH₃ Ia1.421 or Ib1.421 Cl CH₃ H OCH₂CH₃ Ia1.422 or Ib1.422 Cl CH₃ H OCH₂C₆H₅ Ia1.423 or Ib1.423 Cl CH₃ H OCH₂(2-furyl) Ia1.424 or Ib1.424 Cl CH₃ H OCH₂(3-furyl) Ia1.425 or Ib1.425 Cl CH₃ H OCOOCH₃ Ia1.426 or Ib1.426 Cl CH₃ H OCOOCH₂CH₃ Ia1.427 or Ib1.427 Cl CH₃ H OCOOCH(CH₃)₂ Ia1.428 or Ib1.428 Cl CH₃ H OCOOC₆H₅ Ia1.429 or Ib1.429 Cl CH₃ H OCOOC(CH₃)₃ Ia1.430 or Ib1.430 Cl CH₃ H OCSOC₆H₅ Ia1.431 or Ib1.431 Cl CH₃ H OCSN(CH₃)₂ Ia1.432 or Ib1.432 Cl CH₃ H OCON(CH₃)₂ Ia1.433 or Ib1.433 Cl CH₃ H OCOSCH₃ Ia1.434 or Ib1.434 Cl CH₃ H ON(CH₃)₂ Ia1.435 or Ib1.435 Cl CH₃ H O-1-piperidyl Ia1.436 or Ib1.436 Cl CH₃ H OCOCH₃ Ia1.437 or Ib1.437 Cl CH₃ H OCOCH₂CH₃ Ia1.438 or Ib1.438 Cl CH₃ H OCOCH(CH₃)₂ Ia1.439 or Ib1.439 Cl CH₃ H OCOC(CH₃)₃ Ia1.440 or Ib1.440 Cl CH₃ H OCO(CH₂)₆CH₃ Ia1.441 or Ib1.441 Cl CH₃ H OCO(CH₂)₇CH₃ Ia1.442 or Ib1.442 Cl CH₃ H OCO(CH₂)₁₆CH₃ Ia1.443 or Ib1.443 Cl CH₃ H OCO(CH₂)₁₄CH₃ Ia1.444 or Ib1.444 Cl CH₃ H OCOCH₂CH₂CH═CH₂ Ia1.445 or Ib1.445 Cl CH₃ H OCO(CH₂)₃O(2,4-Cl₂—C₆H₃) Ia1.446 or Ib1.446 Cl CH₃ H OCOCH(CH₃)O— (2-CH₃-4-Cl—C₆H₃) Ia1.447 or Ib1.447 Cl CH₃ H OCOcyclopropyl Ia1.448 or Ib1.448 Cl CH₃ H OCOcyclopentyl Ia1.449 or Ib1.449 Cl CH₃ H OCOcyclohexyl Ia1.450 or Ib1.450 Cl CH₃ H OCOC₆H₅ Ia1.451 or Ib1.451 Cl CH₃ H OCO(2-tetrahydrofuryl) Ia1.452 or Ib1.452 Cl CH₃ H OCO(2-furyl) Ia1.453 or Ib1.453 Cl CH₃ H OCO(2-thienyl) Ia1.454 or Ib1.454 Cl CH₃ H OCO(3-pyridyl) Ia1.455 or Ib1.455 Cl CH₃ H OSO₂CH₃ Ia1.456 or Ib1.456 Cl CH₃ H OSO₂CH₂CH₃

Extraordinary preference is furthermore given to the following cyclohexenonequinolinoyl derivatives of the formula I:

-   -   the compounds of the formulae Ia2 and Ib2, in particular the         compounds Ia2.1 to Ia2.456 and the compounds Ib2.1 to Ib2.456,         which differ from the compounds Ia1.1 to Ia1.456 and Ib1.1 to         Ib1.456, respectively, in that (R⁶)₁ is “5,5-dimethyl”.

-   -   the compounds of the formulae Ia3 and Ib3, in particular the         compounds Ia3.1 to Ia3.456 and the compounds Ib3.1 to Ib3.456,         which differ from the compounds Ia1.1 to Ia1.456 and Ib1.1 to         Ib1.456, respectively, in that (R⁶)₁ is “5-methyl”.

-   -   the compounds of the formulae Ia4 and Ib4, in particular the         compounds Ia4.1 to Ia4.456 and the compounds Ib4.1 to Ib4.456,         which differ from the compounds Ia1.1 to Ia1.456 and Ib1.1 to         Ib1.456, respectively, in that (R⁶)₁ is “4,4-dimethyl”.

-   -   the compounds of the formulae Ia5 and Ib5, in particular the         compounds Ia5.1 to Ia5.456 and the compounds Ib5.1 to Ib5.456,         which differ from the compounds Ia1.1 to Ia1.456 and Ib1.1 to         Ib1.456, respectively, in that (R⁶)₁ is “6,6-dimethyl”.

-   -   the compounds of the formulae Ia6 and Ib6, in particular the         compounds Ia6.1 to Ia6.456 and the compounds Ib6.1 to Ib6.456,         which differ from the compounds Ia1.1 to Ia1.456 and Ib1.1 to         Ib1.456, respectively, in that (R⁶)₁ is         “4,4,6,6-tetramethyl-5-oxo”.

-   -   the compounds of the formulae Ia7 and Ib7, in particular the         compounds Ia7.1 to Ia7.456 and the compounds Ib7.1 to Ib7.456,         which differ from the compounds Ia1.1 to Ia1.456 and Ib1.1 to         Ib1.456, respectively, in that (R⁶)₁ is “6-methyl”.

-   -   the compounds of the formulae Ia8 and Ib8, in particular the         compounds Ia8.1 to Ia8.456 and the compounds Ib8.1 to Ib8.456,         which differ from the compounds Ia1.1 to Ia1.456 and Ib1.1 to         Ib1.456, respectively, in that (R⁶)₁ is         “5-hydroxy-4,4,6,6-tetramethyl”.

The cyclohexenonequinolinoyl derivatives of the formula I can be obtained by various routes, for example by the following processes:

A. Preparation of compounds of the formula I where R⁵=halogen by reaction of cyclohexanedione derivatives of the formula III with halogenating agents:

Suitable halogenating agents are, for example, phosgene, diphosgene, triphosgene, thionyl chloride, oxalyl chloride, phosphorus chloride, phosphorus pentachloride, mesyl chloride, chloromethylene-N, N-dimethylammonium chloride, oxalyl bromide, phosphorus oxybromide etc.

B. Preparation of compounds of the formula I where R⁵=OR⁷, OSO₂R⁸, OPR⁸R⁹, OPSR⁸R⁹ or OPSR⁸R⁹ by reaction of cyclohexane dione derivatives of the formula III with alkylating, sulfonylating or phosphonylating agents IVα, IVβ, IVβ, IVδ or IVε.

L¹ is a nucleophilically replaceable leaving group, such as halogen, for example chlorine or bromine, hetaryl, for example imidazolyl, carboxylate, for example acetate, or sulfonate, for example mesylate or triflate, etc.

The compounds of the formula IVα, IVβ, IVγ, IVδ or IVε can be employed directly such as, for example, in the case of the carbonyl halides, or generated in situ, for example activated carboxylic acids (using carboxylic acid and dicyclohexyl carbodiimide, etc.).

C. Preparation of compounds of the formula I where R⁵=OR⁷, SR⁷, POR⁸R⁹, NR¹⁰R¹¹, ONR¹¹R¹², N-linked heterocyclyl or O—(N-linked heterocyclyl) by reaction of compounds of the formula I where R⁵=halogen, OSO₂R⁸ (Iα) with compounds of the formula Vα, Vβ, Vγ, Vδ, Vε, Vηor Vθ, if appropriate in the presence of a base or with prior formation of salt.

D. Preparation of compounds of the formula I where R⁵=SOR⁸, SO₂R⁸ by reaction of compounds of the formula I where R⁵=SR⁸ (Iβ) with an oxidizing agent.

-   -   Suitable oxidizing agents are, for example, m-chloroperbenzoic         acid, peroxy acetic acid, trifluoroperoxy acetic acid, hydrogen         peroxide, if appropriate in the presence of a catalyst such as         tungstate.

The following conditions apply to the abovementioned reactions: The starting materials are generally employed in equimolar amounts. However, it will also be advantageous to employ an excess of one or the other component.

If appropriate, it may be advantageous to carry out the reactions in the presence of a base. Here, the starting materials and the base are advantageously employed in equimolar amounts. An excess of base, for example 1.5 to 3 molar equivalents, based on Ia and/or Ib (where R⁵=halogen or OSO₂R⁸) or III may in certain cases be advantageous.

Suitable bases are tertiary alkyl amines, such as triethylamine, aromatic amines, such as pyridine, alkali metal carbonates, for example sodium carbonate or potassium carbonate, alkali metal bicarbonates, such as sodium bicarbonate and potassium bicarbonate, alkali metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium tert-butoxide or alkali metal hydrides, for example sodium hydride. Preference is given to using triethylamine or pyridine.

Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl-tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as acetonitrile, dimethyl formamide or dimethyl sulfoxide, or esters, such as ethyl acetate, or mixtures of these.

The reaction temperature is generally in the range of from 0° C. to the boiling point of the reaction mixture.

Work-up to give the product can be carried out in a manner known per se.

Depending on the reaction conditions, the compounds Ia, Ib or mixtures of these can be formed. The latter can be separated by classical separation methods, such as, for example, crystallization, chromatography, etc.

The cyclohexanedione derivatives of the formula III are known or can be prepared by processes known per se (for example DE-A 19 532 311), for example by reacting cyclohexanones of the formula VI with an activated benzoic acid VIIa or a benzoic acid VIIb, which is preferably activated in situ, to give the acylation product which is subsequently rearranged.

L² is a nucleophilically replaceable leaving group, such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, carboxylate, for example acetate or trifluoroacetate, etc.

The activated benzoic acid VIIa can be employed directly, such as in the case of the benzoyl halides, or be generated in situ, for example using dicyclohexyl carbodiimide, triphenylphosphine/azodicarboxylic ester, 2-pyridine disulfide/triphenyl phosphine, carbonyldiimidazole, etc.

If appropriate, it may be advantageous to carry out the acylation reaction in the presence of a base. Here, the starting materials and the auxiliary base are advantageously employed in equimolar amounts. A slight excess of the auxiliary base, for example from 1.2 to 1.5 molar equivalents, based on VII, may be advantageous in certain cases.

Suitable auxiliary bases are tertiary alkyl amines, pyridine or alkali metal carbonates. Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene or chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide, or esters, such as ethyl acetate, or mixtures of these.

If the activated carboxylic acid component employed is a benzoyl halide, it may be advantageous to cool the reaction mixture to 0–10° C. on addition of this reaction partner. The mixture is subsequently stirred at 20–100° C., preferably at 25–50° C., until the reaction is complete. Work-up is carried out in a customary manner, for example the reaction mixture is poured into water and the product of value is extracted. Solvents which are suitable for this purpose are, in particular, methylene chloride, diethyl ether and ethyl acetate. The organic phase is dried and the solvent is removed, after which the crude ester can be employed without any further purification for the rearrangement.

The rearrangement of the esters to the compounds of the formula is advantageously carried out at 20–100° C. in a solvent and in the presence of a base and, if appropriate, with the aid of a cyano compound as catalyst.

Suitable solvents are, for example, acetonitrile, methylene chloride, 1,2-dichloroethane, dioxane, ethyl acetate, toluene or mixtures of these. Preferred solvents are acetonitrile and dioxane.

Suitable bases are tertiary amines, such as triethylamine, aromatic amines, such as pyridine, or alkali metal carbonates, such as sodium carbonate or potassium carbonate, which are preferably employed in an equimolar amount, or up to a four-fold excess, based on the ester. Preference is given to using triethylamine or alkali metal carbonate, preferably in twice the equimolar amount, based on the ester.

Suitable cyano compounds are inorganic cyanides, such as sodium cyanide or potassium cyanide, and organic cyano compounds, such as acetone cyanohydrin or trimethylsilyl cyanide. They are employed in an amount from 1 to 50 mol percent, based on the ester. Preference is given to using acetone cyanohydrin or trimethylsilyl cyanide, for example in an amount from 5 to 15, preferably 10, mol percent, based on the ester.

Work-up can be carried out in a manner known per se. For example, the reaction mixture is acidified with dilute mineral acid, such as 5% strength hydrochloric acid, or sulfuric acid, and extracted with an organic solvent, for example methylene chloride or ethyl acetate. The organic extract can be extracted with 5–10% strength alkali metal carbonate solution, for example sodium carbonate or potassium carbonate solution. The aqueous phase is acidified and the resulting precipitate is filtered off with suction and/or extracted with methylene chloride or ethyl acetate, dried and concentrated.

The benzoyl halides of the formula VIIa (where L²=Cl, Br) can be prepared in a manner known per se by reaction of the benzoic acids of the formula VIIb with halogenating agents, such as thionyl chloride, thionyl bromide, phosgene, diphosgene, triphosgene, oxalyl chloride, oxalyl bromide.

The benzoic acids of the formula VIIb can be prepared in a known manner from the corresponding esters by acidic or basic hydrolysis. The latter are known from the literature or can be prepared in a manner known per se.

8-Difluoromethyl-5-alkoxycarbonyl-quinolines can be obtained from the corresponding 8-aldehyde derivatives by fluorination. A suitable fluorinating agent is, inter alia, DAST. The formyl quinoline is obtained by oxidation of the corresponding bromomethyl quinoline.

Furthermore, it is possible to obtain 8-difluoromethoxy-5-alkoxycarbonyl-quinolines from the corresponding 8-hydroxy derivatives by reaction with chlorodifluoromethane. This reaction is preferably carried out in the presence of a base, such as potassium hydroxide or sodium hydroxide, in an aprotic solvent. The 8-hydroxy-5-alkoxycarbonylquinolines are obtained from 8-hydroxy-5-hydroxycarbonyl-quinoline by esterification reactions which are known per se.

PREPARATION EXAMPLES

-   2-[(8-Chloroquinolin-5-yl)carbonyl]-1-chloro-4,4,6,6-tetramethyl-cyclohex-1-ene-3,5-dione     (Compound 2.22) and -   2-[(8-chloroquinolin-5-yl)chloromethylidene]-4,4,6,6-tetramethylcyclohexane-1,3,5-trione     (Compound 3.1) -   4.0 g (10.8 mmol) of     2-(8-chloroquinolin-5-yl)carbonyl-4,4,6,6-tetramethylcyclohexane-1,3,5-trione     were dissolved in 40 ml of dichloromethane, and 4.1 g (32.4 mmol) of     oxalyl chloride and 1.5 ml of dimethylformamide were added. The     mixture was stirred at 25° C. for 1.5 hours, after which the solvent     was removed. This gave 3.9 g of colorless crystals. Silica gel     chromatography (mobile phase: toluene/methyl-tert-butyl ether) gave: -   2-[(8-chloroquinolin-5-yl)carbonyl]-1-chloro-4,4,6,6-tetra-methylcyclohex-1-ene-3,5-dione:     Yield 0.65 g (colorless crystals); m.p.: 180° C.; -   2-[(8-chloroquinolin-5-yl)chloromethylidene-4,4,6,6-tetramethyl-cyclohexane-1,3,5-trione:     Yield: 0.35 g (colorless crystals); m.p.: 156° C. -   2-[(8-Chloroquinolin-5-yl)-1-(4′-oxo-1′,4′-dihydropyrid-1′-yl)-4,4,6,6-tetramethyl-cyclohex-1-ene-3,5-dione     (Compound 2.46) and -   2-[(8-chloroquinolin-5-yl)-(4′-oxo-1′,4′-dihydropyrid-1′-yl)-methylidene]-4,4,6,6-tetramethyl-cyclohexane-1,3,5-trione     (Compound 3.5) -   1.0 g (2.6 mmol) of a mixture of the compounds 2.22 and 3.1 was     dissolved in 25 ml of methylene chloride, 0.82 g (8.7 mmol) of     4-hydroxypyridine were added and the mixture was stirred at 40° C.     for 8 hours. Insoluble components were subsequently filtered off,     the solvent was removed and the residue was chromatographed over     silica gel (mobile phase: methylene chloride/methanol). This gave:     2-[(8-chloroquinolin-5-yl)-4′-oxo-1′,4′-dihydropyridin-1′-yl)methylidene-4,4,6,6-tetramethylcyclohexane-1,3,5-trione:     Yield 0.40 g (colorless oil); -   2-[(8-chloroquinolin-5-yl)carbonyl]-1-(4′-oxo-1′,4′-dihydro-40     pyrid-1′-yl)-4,4,6,6-tetramethylcyclohex-1-ene-3,5-dione: Yield 0.25     g (colorless crystals); m.p.>210° C. -   2-(8-fluoroquinolin-5-yl)carbonyl-1,5-di(ethoxycarbonyloxy)-4,4,6,6-tetramethyl-cyclohex-1-ene-3,5-dione     (Compound 3.20) 0.12 g (4 mmol) of sodium hydride was dissolved in     10 ml of tetrahydrofuran, 0.36 g (1 mmol) of -   2-[(8-fluoroquinolin-5-yl)carbonyl]-4,4,6,6-tetramethyl-1-hydroxy-cyclohexane-3,5-dione     in 5 ml of tetrahydrofuran was added dropwise at room temperature     and the mixture was stirred at 40° C. for 1 hour. At room     temperature, 0.43 g (4 mmol) of ethyl chloroformate were     subsequently added dropwise, and the mixture was heated under reflux     for 3 hours. After cooling, water was added and the mixture was     extracted with ethyl acetate, the organic phase was washed with 2%     strength potassium carbonate solution and water and dried and the     solvent was removed. This gave 0.45 g of a colorless oil). -   2-[(8-Chloroquinolin-5-yl)carbonyl]-1-[(dimethylamino)carbonyl-thio]-4,4,6,6-tetramethyl-cyclo-hex-1-ene-3,5-dione     (Compound 2.45) and -   2-{(8-chloroquinolin-5-yl)-[(dimethylamino)carbonylthio]-methylidene}-4,4,6,6-tetramethylcyclohexane-1,3,5-trione     (Compound 3.4) -   0.50 g (1.3 mmol) of     2-[(8-chloroquinolin-5-yl)carbonyl]4,4,6,6-tetramethyl-cyclohexane-1,3,5-trione     was dissolved in 15 ml of tetrahydrofuran, 0.52 g (5.2 mmol) of     triethylamine was added and 0.32 g (2.6 mmol) of     dimethylaminothiocarbonyl chloride in 5 ml of tetrahydrofuran was     added dropwise. The mixture was stirred at room temperature for 30     hours, the solvent was removed, and the residue was taken up in the     ethyl acetate, washed with 5% strength potassium carbonate solution     and water, dried, concentrated and chromatographed over silica gel     using cyclohexane/ethyl acetate. This gave -   2-[(8-chloroquinolin-5-yl)carbonyl]-1-[(dimethylamino)carbonylthio]-4,4,6,6-tetramethyl-cyclohex-1-ene-3,5-dione:     Yield 0.5 g (colorless crystals); m.p. 138° C.; -   2-{(8-chloroquinolin-5-yl)-[(dimethylamino)carbonyl-thio]methyl-i     dene}-4,4,6,6-tetramethylcyclohexane-1,3,5-trione: Yield: 0.2 g     (colorless crystals) m.p. 75° C. -   2-[(8-difluoromethylquinolin-5-yl)carbonyl]-1-chloro-4,4,6,6-tetramethyl-cyclohex-1-ene-3,5-dione     (Compound 2.31)

Step a) Methyl 8-formyl-5-quinolinecarboxylate

28.8 g (103 mmol) of 8-(bromomethyl)-5-quinolinecarboxylate were dissolved in 200 ml of acetonitrile, 36.1 g (309 mmol) of N-methylmorpholine N-oxide were added, the mixture was stirred at 25° C. for 7 hours and the solvent was then removed. Silica gel chromatography (mobile phase: cyclohexane/ethyl acetate) gave 12.0 g of methyl 8-formyl-5-quinolinecarboxylate (colorless crystals), m.p.: 128° C.

Step b) 8-difluoromethyl-5-quinolinecarboxylate

0.5 g (2.3 mmol) of methyl 8-formyl-5-quinolinecarboxylate was dissolved in 50 ml of dichloroethane and, at −20° C., 1.1 g (6.8 mmol) of diethylaminosulfur trifluoride (DAST) were added dropwise. The mixture was stirred at −20° C. for 30 min and then armed to 25° C., and 50 ml of water were added dropwise. The aqueous phase was extracted with methylene chloride, the combined organic phases were washed with sodium bicarbonate solution and dried and the solvent was removed. Yield: 0.7 g of colorless crystals;

¹H-NMR (δ in ppm, d⁶-DMSO): 9.28 (d, 1H); 9.04 (s, 1H); 8.36 (d, 1H); 8.11 (d, 1H); 7.90 (t, 1H); 7.80 (brd s, 1H); 3.96 (s, 3H).

Step c) 8-difluoromethyl-5-quinolinecarboxylic acid

0.5 g (2.0 mmol) of methyl 8-difluoromethyl-5-quinolinecarboxylate was dissolved in 5 ml of ethanol, 0.43 g (10.5 mmol) of sodium hydroxide and 1 ml of water were added, and the mixture was stirred at 25° C. for 20 hours. The solvents were subsequently removed, the residue was taken up in water, washed twice with methylene chloride and adjusted to pH 1 using 10 N hydrochloric acid, and the precipitate was filtered off with suction. Drying gave 0.5 g of 8-difluoromethyl-5-quinolinecarboxylic acid (colorless crystals);

¹H-NMR (δ in ppm, d⁶-DMSO): 9.35 (d, 1H); 9.04 (s, 1H); 8.38 (d, 1H); 8.10 (d, 1H); 7.92 (t, 1H); 7.78 (brd s, 1H).

Step d) 2-[(8-difluoromethylquinolin-5-yl)carbonyl]-4,4,6,6-tetramethylcyclohexane-1,3,5-trione

0.26 g (1.4 mmol) of 2,2,4,4-tetramethylcyclohexane-1,3,5-trione was dissolved in 10 ml of acetonitrile, 0.34 g (1.4 mmol) of 8-difluoromethyl-5-quinolinecarboxylic acid and 0.38 g (1.9 mmol) of dicyclohexylcarbodiimide were added and the mixture was stirred at 25° C. for 17 hours. 0.57 g (5.6 mmol) of triethylamine and 5 drops of trimethylsilyl cyanide were then added to the suspension, and stirring was continued at 25° C. for a further 25 hours. 50 ml of 5% strength potassium carbonate solution were subsequently added, the mixture was filtered, the filtrate was washed with methyl tert-butyl ether, the aqueous phase was adjusted to pH 2 using concentrated hydrochloric acid and the precipitate was filtered off, washed with water and dried. Yield: 0.25 g (colorless crystals);

¹H-NMR (δ in ppm, CDCl₃): 17.5 (s, 1H); 9.02 (q, 1H); 8.24 (d, 1H); 8.06 (d, 1H); 7.82 (t, 1H); 7.50 (m, 2H); 1.60 (s, 6H); 1.36 (s, 6H).

Step e) 2-[(8-Difluoromethylquinolin-5-yl)carbonyl]-1-chloro-4,4,6,6-tetramethyl-cyclohex-1-ene-3,5-dione (Compound 2.31)

0.25 g (0.65 mmol) of 2-(8-difluoromethylquinolin-5-yl)carbonyl-4,4,6,6-tetramethyl-cyclohexane-1,3,5-trione was dissolved in 15 ml of dichloromethane and 0.25 g (1.95 mmol) of oxalyl chloride and 7 drops of dimethylformamide were added. The mixture was stirred at 25° C. for 17 hours, after which the solvent was removed. This gave 0.2 g of colorless crystals.

Preparation of the Precursor 2-[(8-difluoromethoxyquinolin-5-yl)carbonyl]-4,4,6,6-tetramethylcyclohexane-1,3,5-trione Step a) Methyl 8-hydroxy-5-quinolincarboxylate

16.25 g (86 mmol) of 8-hydroxy-5-quinolinecarboxylic acid were dissolved in 70 ml of methanol, 3 ml of concentrated sulfuric acid were added and the mixture was heated under reflux for 25 hours. The solvent was then removed and the residue was taken up in ice-water, adjusted to a pH of 8 using sodium carbonate solution and filtered hot. The residue was extracted with methyl-tert-butyl ether for 7 hours on a jacketed Soxhlet extractor, and the solvent was subsequently removed from the extract. This gave 6.8 g of a brown powder;

¹H-NMR (δ in ppm, d⁶-DMSO): 9.38 (d, 1H); 8.90 (d, 1H); 8.26 (d, 1H); 7.71 (dd, 1H); 7.15 (d, 1H); 3.93 (s, 3H).

Step b) Methyl 8-difluoromethoxy-5-quinolinecarboxylate

1.0 g (5.0 mmol) of methyl 8-hydroxy-5-quinolinecarboxylate was dissolved in 20 ml of dimethylformamide, 0.76 g (5.5 mmol) of potassium carbonate was added and 14 g of chlorodifluoromethane were introduced at 40° C. over a period of 2 hours. Solid components were then filtered off, the solvent was removed and the residue was washed with water and dried. This gave 0.75 g of a brown powder;

¹H-NMR (δ in ppm, CDCl₃): 9.45 (d, 1H); 9.00 (d, 1H); 8.30 (d, 1H); 7.61 (dd, 1H); 7.49 (d, 1H); 7.18 (t, 1H); 3.99 (s, 3H).

Step c) 8-difluoromethoxy-5-quinolinecarboxylic acid

0.7 g (2.8 mmol) of methyl 8-difluoromethoxy-5-quinolinecarboxylate was suspended in 15 ml of water and 0.4 g (10 mmol) of sodium hydroxide was added. The mixture was stirred at 25° C. for 20 hours and then filtered off, and the filtrate was washed with methyl tert-butyl ether. The aqueous phase was adjusted to pH 3 using concentrated hydrochloric acid and filtered off, and the residue was dried. This gave 0.45 g of a colorless powder;

¹H-NMR (δ in ppm, d⁶-DMSO): 13.5 (br, 1H); 9.39 (d, 1H); 9.03 (d, 1H); 8.32 (d, 1H); 7.78 (dd, 1H); 7.62 (d, 1H); 7.60 (t, 1H).

Step d) 2-[(8-difluoromethoxyquinolin-5-yl)carbonyl]-4,4,6,6-tetramethylcyclohexane-1,3,5-trione

0.4 g (1.7 mmol) of 8-difluoromethoxy-5-quinolinecarboxylic acid was dissolved in 20 ml of acetonitrile, 0.4 g (1.9 mmol) of N,N-dicyclohexylcarbodiimide and 0.3 g (1.7 mmol) of 2,2,4,4-tetramethylcyclohexane-1,3,5-trione were added and the mixture was stirring at 25° C. for 20 hours. 0.4 g (4.0 mmol) of triethylamine and 2 drops of trimethylsilyl cyanide were then added, and stirring was continued at 30–35° C. for a further 3 hours. The precipitate was filtered off, and the filtrate was concentrated, 20 ml of 5% strength potassium carbonate solution were added and the mixture was washed with methyl tert-butyl ether. The aqueous phase was subsequently adjusted to pH 3 using concentrated hydrochloric acid and extracted with ethyl acetate. The solvent was removed and the residue was chromatographed over silica gel (mobile phase: methylene chloride/methanol). This gave 0.2 g of a colorless powder;

35 ¹H-NMR (δ in ppm, CDCl₃): 16.5 (br, 1H); 9.02 (d, 1H); 8.30 (d, 1H); 7.51 (m, 2H); 7.21 (d, 1H); 7.17 (t, 1H); 1.60 (s, 6H); 1.35 (s, 6H).

In addition to the cyclohexenone quinolinoyl derivatives of the formula I described above, further derivatives which were prepared or are preparable in a similar manner or in a manner known per se are listed in Tables 2 and 3:

TABLE 2 Ia

No. R¹ R² R³ R⁵ (R⁶)₁ m.p. [° C.] or ¹H-NMR [ppm] 2.1 F H H OCOC₆H₅ 4,4,6,6-(CH₃)₄-5-oxo 178 2.2 F H H OCOC(CH₃)₃ 4,4,6,6-(CH₃)₄-5-oxo 9.22(d, 1H); 9.03(d, 1H); 7.98(q, 1H); 7.62(q, 1H); 7.39(t, 1H); 1.49 (s, 6H); 1.40(s, 6H); 1.11(s, 9H) 2.3 Cl H H OCOC₆H₅ 4,4,6,6-(CH₃)₄-5-oxo >200 2.4 Cl H H OCOC(CH₃)₃ 4,4,6,6-(CH₃)₄-5-oxo 9.20(dd, 2H); 8.85(q, 2H); 7.60(q, 1H); 1.40(s, 12H); 1.12(s, 9H) 2.5 CH₃ H H OPS(OCH₂CH₃)₂ 4,4,6,6-(CH₃)₄-5-oxo 9.50(d, 1H); 8.98(d, 1H); 8.06(d, 1H); 7.60(m, 2H); 3.95(m, 4H); 2.90 (s, 3H); 1.65(s, 6H); 1.51(s, 6H) 2.6 CH₃ H H OCOSCH₃ 4,4,6,6-(CH₃)₄-5-oxo 128 2.7 CH₃ H H OCSN(CH₃)₂ 4,4,6,6-(CH₃)₄-5-oxo 163 2.8 CH₃ H H OCOC₆H₅ 4,4,6,6-(CH₃)₄-5-oxo 9.05(d, 1H); 9.85(d, 1H); 7.92(d, 1H); 7.72(d, 2H); 7.51(d, 1H); 7.48 (t, 1H); 7.35(q, 1H); 7.28(t, 2H); 2.79(s, 3H); 1.62(s, 6H); 1.55(s, 6H) 2.9 CH₃ H H OPO[N(CH₃]₂ 4,4,6,6-(CH₃)₄-5-oxo 9.41(d, 1H); 8.95(d, 1H); 8.07(d, 1H); 7.58(d, 1H); 7.50(q, 1H); 2.88 (s, 3H); 2.45(s, 6H); 2.42(s, 6H); 1.65(s, 6H); 1.48(s, 6H) 2.10 CH₃ H H OCO(CH₂)₃O(2,4- 4,4,6,6-(CH₃)₄-5-oxo oil Cl2-C₆H₃) 2.11 CH₃ H H OCOCH(CH₃)O(2-CH₃- 4,4,6,6-(CH₃)₄-5-oxo oil 4-Cl—C₆H₃) 2.12 CH₃ H H OCOC(CH₃)₃ 4,4,6,6-(CH₃)₄-5-oxo 9.20(d, 1H); 8.85(d, 1H); 7.80(d, 1H); 7.51(d, 1H); 7.48(q, 1H); 2.85 (s, 3H); 1.55(s, 6H); 1.50(s, 6H); 1.08(s, 9H) 2.13 F H H OCOC(CH₃)₃ 4,4,6-(CH₃)₃ oil 2.14 Cl H H OCOCH₂CH₃ 4,4,6,6-(CH₃)₄-5-oxo 9.13(d, 1H); 9.02(d, 1H); 7.85(s, 2H); 7.58(q, 1H); 2.40(q, 2H); 1.60 (s, 6H); 1.50(s, 6H); 1.05(t, 3H) 2.15 F H H OCOSCH₃ 4,4,6,6-(CH₃)₄-5-(OH) 190–192 2.16 Cl H H OCOSCH₃ 4,4,6,6-(CH₃)₄-5-oxo  84 2.17 F H H OCOSCH₃ 4,4,6,6-(CH₃)₄-5-oxo  72 2.18 CH₃ H H OCH₃ 4,4,6,6-(CH₃)₄-5-oxo 9.44(d, 1H); 9.03(d, 1H); 7.88(d, 1H); 7.59(m, 2H); 3.92(s, 3H); 2.90 (s, 3H); 1.50(s, 6H); 1.38(s, 6H) 2.19 F H H OSO₂CH₃ 4,4,6,6-(CH₃)₄-5-(OH) 9.30(d, 1H); 9.02(d, 1H); 7.93(q, 1H); 7.61(q, 1H); 7.40(q, 1H); 3.01 (s, 3H); 1.57(s, 3H); 1.53(s, 3H); 1.32(s, 3H); 1.28(s, 3H) 2.20 F H H OCOOCH₂CH₃ 4,4,6,6-(CH₃)₄-5- 9.18(d, 1H); 9.02(s, 1H); 7.92(q, (OCOOCH₂CH₃) 1H); 7.65(q, 1H); 7.41(q, 1H); 4.32 (q, 2H); 4.11(q, 1H); 1.45(s, 3H); 1.40(s, 3H); 1.38(s, 3H); 1.30(s, 3H); 1.22(s, 3H); 1.15(s, 3H) 2.21 F H H OCH₃ 4,4,6,6-(CH₃)₄-5-oxo 9.45(d, 1H); 9.03(d, 1H); 7.96(q, 1H); 7.68(q, 1H); (7.40(t, 1H); 3.88(s, 3H); 1.50(s, 6H); 1.39(s, 6H) 2.22 Cl H H Cl 4,4,6,6-(CH₃)₄-5-oxo 180 2.23 F H H Cl 4,4,6,6-(CH₃)₄-5-oxo 152 2.24 Cl H H S(4-CH₃—C₆H₄) 4,4,6,6-(CH₃)₄-5-oxo 119 2.25 S(4-CH₃— H H S(4-CH₃—C₆H₄) 4,4,6,6-(CH₃)₄-5-oxo 132–135 C₆H₄) 2.26 Cl H H Cl 4,4,6,6-(CH₃)₄-5-oxo 2.27 O(tetra- H H Cl 4,4,6,6-(CH₃)₄-5-oxo 9.65(d, 1H); 9.05(d, 1H); 8.83(d, hydro- 1H); 7.66(q, 1H); 6.95(d, 1H); 5.23 furan- (m, 1H); 4.21(d, 2H); 4.05(m, 2H); 3-yl) 2.39(m, 2H); 1.62(s, 6H); 1.48(s, 6H) 2.28 CH₃ H H Cl 4,4,6,6-(CH₃)₄-5-oxo 194 2.29 F H H Cl 4,4,6-(CH₃)₃ oil 2.30 CH₃ H H Br 4,4,6,6-(CH₃)₄-5-oxo oil 2.31 CHF₂ H H Cl 4,4,6,6-(CH₃)₄-5-oxo 9.40(d, 1H); 9.05(d, 1H); 8.05(d, 1H); 7.86(t, 1H); 7.80(d, 1H); 7.65 (q, 1H); 1.59(s, 6H); 1.48(s, 6H) 2.32 CF₃ H H Cl 4,4,6,6-(CH₃)₄-5-oxo oil 2.33 CF₃ CH₃ H Cl 5,5-(CH₃)₂ 9.15(d, 1H); 8.10(d, 1H); 7.75(d, 1H); 7.52(d, 1H); 3.02(s, 2H); 2.91 (s, 2H); 2.80(s, 3H); 1.20(s, 6H) 2.34 CH₃ H H N(CH₃)OCH₃ 4,4,6,6-(CH₃)₄-5-oxo oil 2.35 CH₃ H H SCH₃ 4,4,6,6-(CH₃)₄-5-oxo 9.50(d, 1H); 9.02(d, 1H); 7.80(d, 1H); 7.50(m, 3H); 2.90(s, 3H); 2.30 (s, 3H); 1.50(s, 6H); 1.35(s,3H); 1.25(s, 3H) 2.36 Cl H H 1-pyrazolyl 4,4,6,6-(CH₃)₄-5-oxo 9.30(d, 1H); 9.05(d, 1H); 7.80(d, 1H); 7.75(d, 1H); 7.61(q, 1H); 7.52 (d, 1H); 7.40(s, 1H); 6.11(s, 1H); 1.65(s, 3H); 1.60(s, 3H); 1.50(s, 6H) 2.37 Cl H H N(CH₃)OCH₃ 4,4,6,6-(CH₃)₄-5-oxo 190 2.38 CH₃ H H 1-pyrolidinyl 4,4,6,6-(CH₃)₄-5-oxo oil 2.39 CH₃ H H 4-morpholinyl 4,4,6,6-(CH₃)₄-5-oxo 205 2.40 Cl H H 4-morpholinyl 4,4,6,6-(CH₃)₄-5-oxo 205 2.41 CH₃ H H Cl 4,4,6,6-(CH₃)₄-5-oxo 194 2.42 CH₃ H H 1-pyrazolyl 4,4,6,6-(CH₃)₄-5-oxo 150 2.43 CF₃ H H 4-morpholinyl 4,4,6,6-(CH₃)₄-5-oxo oil 2.44 CHNOCH₃ H H Cl 4,4,6,6-(CH₃)₄-5-oxo oil 2.45 Cl H H SCON(CH₃)₂ 4,4,6,6-(CH₃)₄-5-oxo 138 2.46 Cl H H 4-oxo-1,4-dihydro- 4,4,6,6-(CH₃)₄-5-oxo >210 pyrid-1-yl 2.47 F H H Cl 4,6-(CH₃)₂-4-SCH₃ oil 2.48 CH₃ H H SCON(CH₃)₂ 4,4,6,6-(CH₃)₄-5-oxo 166 2.49 CH₃ H H OP(OCH₂CH₃)₂ 4,4,6,6-(CH₃)₄-5-oxo 9.65(d, 1H); 8.97(d, 1H); 7.79(d, 1H); 7.60(m, 2H); 4.00(m, 4H); 2.91 (s, 3H); 1.71(s, 6H); 1.51(s, 6H) 2.50 OCH₃ H H Cl 4,4,6,6-(CH₃)₄-5-oxo 9.65(d, 1H); 9.01(d, 1H); 7.83(d, 1H); 7.65(q, 1H); 7.02(d, 1H); 4.18 (s, 3H); 1.65(s, 6H); 1.55(s, 6H) 2.51 F H H OCOS(CH₂)₇CH₃ 4,4,6,6-(CH₃)₄-5-oxo 9.20((d, 1H); 9.02(d, 1H); 7.89 (q, 1H); 7.60(q, 1H); 7.40(t, 1H); 2.62(t, 2H); 1.55(s, 6H); 1.48(s, 6H); 1.1–1.5(m, 12H); 0.85(t, 3H) 2.52 F H H Cl 4,6-(ethan-1,2-diyl)¹⁾ 9.55(d, 1H); 9.02(d, 1H); 7.78 (q, 1H); 7.65(q, 1H); 7.40(t, 1H); 3.24(m, 1H); 3.17(m, 1H); 2.41(d, 1H); 1.8–2.4(m, 5H) 2.53 SCH₃ H H OCOSCH₃ 4,4,6,6-(CH₃)₄-5-oxo 147 2.54 F H H OCOSCH₂CH₃ 4,4,6,6-(CH₃)₄-5-oxo 107 2.55 Br H H OCOC(CH₃)₃ 4,4,6,6-(CH₃)₄-5-oxo 134 2.56 Br H H OCO(C₆H₅) 4,4,6,6-(CH₃)₄-5-oxo 228 2.57 Cl H H F 4,4,6,6-(CH₃)₄-5-oxo 181 2.58 F H H SO₂CH₃ 4,4,6,6-(CH₃)₄-5-oxo 206 2.59 F H H SOCH₃ 4,4,6,6-(CH₃)₄-5-oxo 190 2.60 SCH₂F H H F 4,4,6,6-(CH₃)₄-5-oxo 9.50(d, 1H); 9.00(d, 1H); 7.81 (s, 2H); 7.65(g, 1H); 6.01(d, 2H); 1.60(s, 6H); 1.51(s, 6H) 2.61 F H H SC₆H₅ 4,4,6,6-(CH₃)₄-5-oxo  65 2.62 F H H SO₂C₆H₅ 4,4,6,6-(CH₃)₄-5-oxo 111 2.63 F H H SCH₃ 4,4,6,6-(CH₃)₄-5-oxo 143 2.64 CHF₂ H H F 4,4,6,6-(CH₃)₄-5-oxo 183 2.65 Cl CHF₂ H F 4,4,6,6-(CH₃)₄-5-oxo 173 2.66 F H H F 4,4,6,6-(CH₃)₄-5-oxo 153 ¹⁾R⁴ = 4-Oxo-(bicyclo[3.2.1]oct-2-en-3-yl)carbonyl

TABLE 3 Ib

No. R¹ R² R³ R⁵ R⁶ m.p. [° C.] or ¹H-NMR [ppm] 3.1 Cl H H Cl 4,4,6,6-(CH₃)₄-5-oxo 156 3.2 CH₃ H H 1-(1,2,4-triazolyl) 4,4,6,6-(CH₃)₄-5-oxo 9.00(d, 1H); 8.09(s, 1H); 7.82(d, 1H); 7.72(s, 1H); 7.68(d, 1H); 7.47 (d, 1H); 7.35(q, 1H); 2.95(s, 3H); 1.55(s, 6H); 1.30(s, 6H) 3.3 Cl H H 4-morpholinyl 4,4,6,6-(CH₃)₄-5-oxo 9.15(d, 1H); 8.32(d, 1H); 7.82(d, 1H); 7.60(q, 1H); 7.45(d, 1H); 4.05 (m, 2H); 3.68(m, 4H); 3.35(m, 1H); 3.25(m, 1H); 1.30(s, 6H); 1.22(s, 6H) 3.4 Cl H H SCON(CH₃)₂ 4,4,6,6-(CH₃)₄-5-oxo  75 3.5 Cl H H 4-oxo-1,4-dihydro- 4,4,6,6-(CH₃)₄-5-oxo 9.02(d, 1H); 8.42(d, 1H); 7.80(2d, pyrid-1-yl 3H); 7.50(q, 1H); 7.38(d, 1H); 6.72 (d, 2H); 1.50(s, 12H) 3.6 Cl H H N(CH₃)₂ 4,4,6,6-(CH₃)₄-5-oxo 190

The compounds of the formula I and their agriculturally useful salts are suitable, both in the form of isomer mixtures and in the form of the pure isomers, as herbicides. The herbicidal compositions comprising compounds of the formula I control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and harmful grasses in crops such as wheat, rice, maize, soya and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.

Depending on the application method used, the compounds of the formula I, or the compositions comprising them, can additionally be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds of the formula I may also be used in crops which tolerate the action of herbicides owing to breeding, including genetic engineering methods.

The compounds of the formula I, or the herbicidal compositions comprising them, can be used for example in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly-concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting or granules, by means of spraying, atomizing, dusting, broadcasting or watering. The use forms depend on the intended aims; in any case, they should guarantee a very fine distribution of the active compounds according to the invention.

The herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or of an agriculturally useful salt of I, and auxiliaries which are customary for the formulation of crop protection agents.

Essentially, suitable inert auxiliaries include: mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, or strongly polar solvents, e.g. amines such as N-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the cyclohexenonequinolinoyl derivatives of the formula I, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates comprising active substance, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.

Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, e.g. ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene, or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite waste liquors or methylcellulose. Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate and ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the compounds of the formula I in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise from about 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active compound. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

The following formulation examples illustrate the production of such preparations:

I. 20 parts by weight of the compound No. 2.2 are dissolved in a mixture composed of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate and 5 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.

II. 20 parts by weight of the compound No. 2.4 are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.

III. 20 parts by weight of the compound No. 2.16 are dissolved in a mixture composed of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210 to 280° C. and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.

IV. 20 parts by weight of the compound No. 2.18 are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalenesulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which comprises 0.1% by weight of the active compound.

V. 3 parts by weight of the compound No. 2.22 are mixed with 97 parts by weight of finely divided kaolin. This gives a dust which comprises 3% by weight of the active compound.

VI. 20 parts by weight of the compound No. 2.46 are mixed intimately with 2 parts by weight of the calcium salt of dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenol/urea/formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. This gives a stable oily dispersion.

VII. 1 part by weight of the compound No. 3.1 is dissolved in a mixture composed of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. This gives a stable emulsion concentrate.

VIII. 1 part by weight of the compound No. 3.4 is dissolved in a mixture composed of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol® EM 31 (nonionic emulsifier based on ethoxylated castor oil). This gives a stable emulsion concentrate.

The compounds of the formula I or the herbicidal compositions can be applied pre- or post-emergence. If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that they come into contact as little as possible, if at all, with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).

The application rates of the compound of the formula I are from 0.001 to 3.0, preferably 0.01 to 1.0 kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage.

To widen the activity spectrum and to achieve synergistic effects, the cyclohexenonequinolinoyl derivatives of the formula I may be mixed with a large number of representatives of other herbicidal or growth-regulating active compound groups and then applied concomitantly. Suitable components for mixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, (het)aryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-aroyl-1,3-cyclohexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexenone oxime ether derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.

It may furthermore be advantageous to apply the compounds of the formula I, alone or else concomitantly in combination with other herbicides, in the form of a mixture with other crop protection agents, for example together with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates may also be added.

Use Examples

The herbicidal activity of the cyclohexenonequinolinoyl derivatives of the formula I was demonstrated by the following greenhouse experiments:

The culture containers used were plastic pots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.

For the pre-emergence treatment, the active compounds, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants, unless this was adversely affected by the active compounds.

For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active compounds which had been suspended or emulsified in water. The test plants were for this purpose either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment. The application rate for the post-emergence treatment was 0.25 or 0.125 kg of a.s. (active substance)/ha.

Depending on the species, the plants were kept at 10–25° C. or 20–35° C. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

The evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial parts and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments are composed of the following species:

Scientific Name Common Name Abutilon theophrasti velvet leaf Chenopodium album lambsquarters Galium aparine catchweed bedstraw Ipomoea spp. morning glory Setaria faberi giant foxtail Setaria viridis green foxtail Solanum nigrum black nightshade

At application rates of 0.25 and 0.125 kg of a.s./ha, the compounds 2.2, 2.4 and 2.16, applied post-emergence, showed very good activity against harmful plants such as giant foxtail, green foxtail and black nightshade. Furthermore, the compounds 2.2 and 2.4 controlled velvet leaf and morning glory very efficiently. Compound 2.16 additionally showed excellent activity against the weeds lambsquarters and catchweed bedstraw. 

1. A cyclohexenonequinolinoyl compound of the formula I

where: R¹ is hydrogen, nitro, halogen, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₁–C₆-alkoxyiminomethyl, C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio, C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl, C₁–C₆-alkylsulfonyl, C₁–C₆-haloalkylsulfonyl, aminosulfonyl, N—(C₁–C₆-alkyl)aminosulfonyl, N, N-di-(C₁–C₆-alkyl) aminosulfonyl N—(C₁–C₆-alkylsulfonyl)amino, N—(C₁–C₆-haloalkylsulfonyl)amino, N—(C₁–C₆-alkyl)-N-(C₁–C₆-alkylsulfonyl)amino, N—(C₁–C₆-alkyl)-N-(C₁–C₆-haloalkylsulfonyl)amino, phenoxy, or phenylthio the four last-mentioned radicals may be partially or fully halogenated and/or may carry one to two of the following substituents: nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or C₁–C₄-haloalkoxy; R², R³ are hydrogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl or halogen; R⁴ is a compound IIa or IIb

where R⁵ is halogen, OR⁷, SR⁷, SOR⁸, SO₂R⁸, OSO₂R⁸, POR⁸R⁹, OPR⁸R⁹, OPOR⁸R⁹, OPSR⁸R⁹, NR¹⁰R¹¹, ONR¹¹R¹² R⁶ is nitro, halogen, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl, di-(C₁–C₆-alkoxy)methyl, di-(C₁–C₆-alkylthio)methyl, (C₁–C₆-alkoxy)(C₁–C₆-alkylthio)methyl, hydroxyl, C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkoxycarbonyloxy, C₁–C₆-alkylthio, C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl, C₁–C₆-alkylsulfonyl, C₁–C₆-haloalkylsulfonyl, C₁–C₆-alkylcarbonyl, C₁–C₆-haloalkylcarbonyl, C₁–C₆-alkoxycarbonyl or C₁–C₆-haloalkoxycarbonyl; or two radicals, which are linked to the same carbon, together form an —O—(CH₂)_(m)—O—, —O—(CH₂)_(m)—S—, —S—(CH₂)_(m)—S—, —O—(CH₂)_(n)— or —S—(CH₂)_(n) chain which is unsubstituted or substituted by one to three radicals from the following group: halogen, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl or C₁–C₄alkoxycarbonyl; or two radicals, which are linked to the same carbon, together form a —(CH₂)_(p) chain which possibly is interrupted by oxygen or sulfur and/or is unsubstituted or substituted by one to four radicals from the following group: halogen, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl or C₁–C₄alkoxycarbonyl; or two radicals, which are linked to the same carbon, together form a methylidene group which is unsubstituted or substituted by one or two radicals from the following group: halogen, hydroxyl, formyl, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio, C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl, C₁–C₆-alkylsulfonyl or C₁–C₆-haloalkylsulfonyl; or two radicals, which are linked to the same carbon, together with this carbon form a carbonyl group; or two radicals, which are linked to different carbons, together form a —(CH₂)_(n) chain which is unsubstituted or substituted by one to three radicals from the following group: halogen, C₁–C₆-alkyl, C₁–C₆-alkoxy, hydroxyl or C₁–C₆-alkoxycarbonyl; R⁷ is C₁–C₆-alkyl, C₃–C₁-alkenyl, C₃–C₆-haloalkenyl, C₃–C₆-alkynyl, C₃–C₆-haloalkynyl, C₃–C₆-cyloalkyl, C₁–C₂₀-alkylcarbonyl, C₂–C₆-alkenylcarbonyl, C₂–C₆-alkynylcarbonyl, C₃–C₆-cyloalkylcarbonyl, C₁–C₆-alkoxycarbonyl, C₃–C₆-alkenyloxycarbonyl, C₃–C₆-alkynyloxycarbonyl, (C₁–C₂₀-alkylthio)carbonyl, C₁–C₆-alkylaminocarbonyl, C₃–C₆-alkenylaminocarbonyl, C₃–C₆-alkynylaminocarbonyl, N,N-di-(C₁–C₆-alkyl)aminocarbonyl, N—(C₃–C₆-alkenyl)-N-(C₁–C₆-alkyl) aminocarbonyl N—(C₃–C₆alkynyl)-N-(C₁–C₆-alkyl) aminocarbonyl, N—(C₁–C₆-alkoxy)-N-(C₁–C₆-alkyl) aminocarbonyl, N—(C₃–C₆-alkenyl)-N-(C₁–C₆-alkoxy) aminocarbonyl, N—(C₃–C₆-alkynyl)-N-(C₁–C₆-alkoxy) aminocarbonyl, di-(C₁–C₆-alkyl)-aminothiocarbonyl, C₁–C₆-alkylcarbonyl-C₁–C₆-alkyl, C₁–C₆-alkoxyimino-C₁–C₆-alkyl, N—(C₁–C₆-alkylamino) imino-C₁–C₆-alkyl or N,N-di-(C₁–C₆-alkylamino)imino-C₁–C₆-alkyl, it being possible for the above-mentioned alkyl, cycloalkyl and alkoxy radicals to be partially or fully halogenated and/or to carry one to three of the following groups: cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio, di-(C₁–C₄-alkyl)amino, C₁–C₄-alkylcarbonyl, C₁–C₄-alkoxycarbonyl, C₁–C₄-alkoxy-C₁–C₄-alkoxycarbonyl, di-(C₁–C₄-alkyl)amino-C₁–C₄-alkoxycarbonyl, hydroxycarbonyl, C₁–C₄-alkylaminocarbonyl, di-(C₁–C₄-alkyl)aminocarbonyl, aminocarbonyl, C₁–C₄-alkylcarbonyloxy or C₃–C₆-cycloalkyl; phenyl, phenyl-C₁–C₆-alkyl, phenylcarbonyl-C₁–C₆-alkyl, phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl, phenoxy-C₁–C₁-alkylcarbonyl, phenylaminocarbonyl, N—(C₁–C₆-alkyl)-N-(phenyl)aminocarbonyl, or phenyl-C₂–C₈-alkenylcarbonyl, the phenyl radical of the 10 last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁–C₄-alkyl, C₁–C₄-halogenalkyl, C₁–C₄-alkoxy or C₁–C₄-haloalkoxy; R⁸,R⁹ are C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-haloalkenyl, C₃–C₆-alkynyl, C₃–C₆-haloalkynyl, C₃–C₆-cycloalkyl, hydroxyl, C₁–C₆-alkoxy, amino, C₁–C₆-alkylamino, C₁–C₆-haloalkylamino, di-(C₁–C₈-alkyl)amino or di-(C₁–C₆-haloalkyl)amino, it being possible for the abovementioned alkyl, cycloalkyl and alkoxy radicals to be partially or fully halogenated and/or to carry one to three of the following groups: cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio, di-(C₁–C₄-alkyl)amino, C₁–C₄-alkylcarbonyl, C₁–C₄-alkoxycarbonyl, C₁–C₄-alkoxy-C₁–C₄-alkoxycarbonyl, di-(C₁–C₄-alkyl)amino-C₁–C₄-alkoxycarbonyl, hydroxycarbonyl, C₁–C₄-alkylaminocarbonyl, di-(C₁–C₄alkyl)aminocarbonyl, aminocarbonyl, C₁–C₄-alkylcarbonyloxy or C₃–C₆-cycloalkyl; phenyl, phenyl-C₁–C-alkyl, phenoxy, the phenyl radical of the last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or C₁–C₄-haloalkoxy; R¹⁰ is C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-haloalkenyl, C₃–C₆-alkynyl, C₃–C₆-haloalkynyl, C₃–C₆-cycloalkyl, hydroxyl, C₁–C₆-alkoxy, C₃–C₆-alkenyloxy, C₃–C₆-alkynyloxy, amino, C₁–C₆-alkylamino, di-(C₁–C₆-alkyl)amino or C₁–C₆-alkylcarbonylamino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three radicals from the following group: cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio, di-(C₁–C₄-alkyl)amino, C₁–C₄-alkylcarbonyl, C₁–C₄-alkoxycarbonyl, C₁–C₄-alkoxy-C₁–C₄-alkoxycarbonyl, di-(C₁–C₄-alkyl)amino-C₁–C₄-alkoxycarbonyl, hydroxycarbonyl, C₁–C₄-alkylaminocarbonyl, di-(C₁–C₄-alkyl)aminocarbonyl, aminocarbonyl, C₁–C₄-alkylcarbonyloxy or C₃–C₆-cycloalkyl; phenyl, or phenyl-C₁–C₆-alkyl, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or C₁–C₄-haloalkoxy; R¹¹,R¹² are C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-alkynyl or C₁–C₆-alkylcarbonyl; l is 0 to 6; m is 2 to 4; n is 1 to 5; p is 2 to 5; and their agriculturally useful salts.
 2. A cyclohexenonequinolinoyl compound of the formula I as claimed in claim 1 where R¹ is halogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₁–C₆-alkoxy, C₁–C₆-alkylthio, or phenylthio, the last-mentioned radical may be partially or fully halogenated and/or may carry one to two of the substituents mentioned below: nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or C₁–C₄-haloalkoxy; R⁵ is halogen, OR⁷, SR⁷, SOR⁸, SO₂R⁸, OSO₂R⁸, OPR⁸R⁹, OPOR⁸R⁹ OPSR⁸R⁹, NR¹⁰R¹¹ or N-bonded heterocyclyl.
 3. A cyclohexenonequinolinoyl compound of the formula I as claimed in claim 1, where R⁵ is halogen, OR⁷, NR¹⁰R¹¹ or N-bonded heterocyclyl.
 4. A cyclohexenonequinolinoyl compound of the formula I as claimed in claim 1, where R⁷ is C₁–C₆-alkyl, C₁–C₂₀alkylcarbonyl, C₁–C₆-alkoxycarbonyl, (C₁–C₂₀-alkylthio)carbonyl, N,N-di-(C₁–C₆-alkyl)aminocarbonyl, phenyl, phenylcarbonyl or phenoxy-C₁–C₆-alkylcarbonyl, it being possible for the phenyl radical of the three last-mentioned substituents to be partially or fully halogenated and/or to carry one to three of the following radicals: nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or C₁–C₄-haloalkoxy; R¹⁰ is C₁–C₆-alkyl or C₁–C₆-alkoxy; R¹¹ is C₁–C₆-alkyl.
 5. A cyclohexenonequinolinoyl compound of the formula I as claimed in claim 1, where R⁶ is nitro, halogen, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl, di-C₁-C₆-alkoxy)methyl, di-(C₁–C₆-alkylthio)methyl, (C₁–C₆-alkoxy)(C₁–C₆-alkylthio)-methyl, hydroxyl, C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkoxycarbonyloxy, C₁–C₆-alkylthio, C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl, C₁–C₆-alkylsulfonyl, C₁–C₆-haloalkylsulfonyl, C₁–C₆-alkylcarbonyl, C₁–C₆-haloalkylcarbonyl, C₁–C₆-alkoxycarbonyl or C₁–C₆-haloalkoxycarbonyl; or two radicals, which are linked to the same carbon, together form an —O—(CH₂)_(m)—O—, —O—(CH₂)_(m)—S—, —S—(CH₂)_(m)—S—, —O—(CH₂)_(n)— or —S—(CH₂)_(n) chain which is unsubstituted or substituted by one to three radicals from the following group: halogen, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl or C₁–C₄-alkoxycarbonyl; or two radicals, which are linked to the same carbon, together form a —(CH₂)_(p) chain which may be interrupted by oxygen or sulfur and which is unsubstituted or substituted by one to four radicals from the following group: halogen, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl or C₁–C₄-alkoxycarbonyl; or two radicals, which are linked to the same carbon, together with this carbon form a carbonyl group.
 6. A process for preparing compounds of the formula I as claimed in claim 1 where R⁵=halogen, which comprises reacting a cyclohexanedione derivative of the formula III,

where the variables R¹ to R³, and I are each as defined in claim 1, with a halogenating agent.
 7. A process for preparing compounds of the formula I as claimed in claim 1 where R⁵=OR⁷, OSO₂R⁸, OPR⁸R⁹, OPOR⁸R⁹ or OPSR⁸R⁹, which comprises reacting a cyclohexanedione derivative of the formula III,

where the variables R¹ to R³, and I are each as defined in claim 1, with a compound of the formula IVα, IVβ, IVγ, Ivδ or IVε, L¹—R⁷  (IVα) L¹—SO₂R⁸  (IVβ) L¹—PR⁸R⁹  (IVγ) L¹—POR⁸R⁹  (IVδ) L¹—PSR⁸R⁹  (IVε) where the variables R⁷ to R⁹ are each as defined in claim 1 and L¹ is a nucleophilically replaceable leaving group.
 8. A process for preparing compounds of the formula I as claimed in claim 1 where R⁵=OR⁷, SR⁷, POR⁸R⁹, NR¹⁰R¹¹, ONR¹¹R¹², or N-linked heterocyclyl, which comprises reacting a compound of the formula I α(≡I where R⁵=halogen, OSO₂R⁸),

I where R⁵=halogen or OSO₂R⁸ where the variables R¹ to R³, R⁵ and I are each as defined in claim 1, with a compound of the formula Vα, Vβ, Vγ, Vδ, Vε, Vη, Vθ, HOR⁷  (Vα) HSR⁷  (Vβ) HPOR⁸R⁹  (Vγ) HNR¹⁰R¹¹  (Vδ) HONR¹¹R¹²  (Vε) H(N-linked heterocyclyl) Vη where the variables R⁷ to R¹² are each as defined in claim 1, if appropriate in the presence of a base.
 9. A process for preparing compounds of the formula I as claimed in claim 1, where R⁵=SOR⁸, SO₂R⁸, which comprises reacting a compound of the formula Iβ (≡I where R⁵=SR⁸),

I where R⁵=SR⁶ where the variables R¹ to R⁸ and I are each as defined in claim 1, with an oxidizing agent.
 10. A composition, comprising a herbicidally effective amount of at least one cyclohexenonequinolinoyl compound of the formula I or an agriculturally useful salt of formula I as claimed in claim 1 and auxiliaries which are conventionally used for formulating crop protection agents.
 11. A process for preparing a composition as claimed in claim 10, which comprises mixing a herbicidally effective amount of at least one cyclohexenonequinolinoyl derivative of the formula I or an agriculturally useful salt of formula I and auxiliaries which are conventionally used for formulating crop protection agents.
 12. A method for controlling undesirable vegetation, which comprises allowing a herbicidally effective amount of at least one cyclohexenonequinolinoyl derivative of the formula I or an agriculturally useful salt of formula I as claimed in claim 1 to act on plants, their habitat and/or on seeds.
 13. A cyclohexenonequinolinoyl compound of the formula I

where: R¹ is hydrogen, nitro, halogen, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₁–C₆-alkoxyiminomethyl, C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio, C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl, C₁–C₆-alkylsulfonyl, C₁–C₆-haloalkylsulfonyl, aminosulfonyl, N—(C₁–C₆-alkyl)aminosulfonyl, N, N-di-(C₁–C₆-alkyl) aminosulfonyl, N—(C₁–C₆-alkylsulfonyl)amino, N—(C₁–C₆-haloalkylsulfonyl)amino, N—(C₁–C₆-alkyl)-N-(C₁–C₆-alkylsulfonyl)amino, N—(C₁–C₆-alkyl)-N-(C₁–C₆-haloalkylsulfonyl)amino, phenoxy, or phenylthio, the two last-mentioned radicals may be partially or fully halogenated and/or may carry one to two of the following substituents: nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or C₁–C₄-haloalkoxy; R², R³ are hydrogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl or halogen; R⁴ is a compound IIa

where R⁵ is halogen, OR⁷, SR⁷, SOR⁸, SO₂R⁸, OSO₂R⁸, POR⁸R⁹, OPR⁸R⁹, OPOR⁸R⁹, OPSR⁸R⁹, NR¹⁰R¹¹, ONR₁₁R¹², N-linked heterocyclyl R⁶ is nitro, halogen, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl, di-(C₁–C₆-alkoxy)methyl, di-(C₁–C₆-alkylthio)methyl, (C₁–C₆-alkoxy)(C₁–C₆-alkylthio)methyl, hydroxyl, C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkoxycarbonyloxy, C₁–C₆-alkylthio, C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl, C₁–C₆-alkylsulfonyl, C₁–C₆-haloalkylsulfonyl, C₁–C₆-alkylcarbonyl, C₁–C₆-haloalkylcarbonyl, C₁–C₆-alkoxycarbonyl or C₁–C₆-haloalkoxycarbonyl; or two radicals, which are linked to the same carbon, together form an —O—(CH₂)_(m)—O—, —O—(CH₂)_(m)—S—, —S—(CH₂)_(m)—S—, —O—(CH₂)_(n)- or —S—(CH₂)_(n) chain which is unsubstituted or substituted by one to three radicals from the following group: halogen, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl or C₁–C₄alkoxycarbonyl; or two radicals, which are linked to the same carbon, together form a —(CH₂)P chain which may be interrupted by oxygen or sulfur and/or is unsubstituted or substituted by one to four radicals from the following group: halogen, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl or C₁–C₄-alkoxycarbonyl; or two radicals which are linked to the same carbon, together form a methylidene group which is unsubstituted or substituted by one or two radicals from the following group: halogen, hydroxyl, formyl, cyano, C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₁–C₆-alkoxy, C₁–C₆-haloalkoxy, C₁–C₆-alkylthio, C₁–C₆-haloalkylthio, C₁–C₆-alkylsulfinyl, C₁–C₆-haloalkylsulfinyl, C₁–C₆-alkylsulfonyl or C₁–C₆-haloalkylsulfonyl; or two radicals, which are linked to the same carbon, together with this carbon form a carbonyl group; or two radicals, which are linked to different carbons, together form a —(CH₂)_(n) chain which is unsubstituted or substituted by one to three radicals from the following group: halogen, C₁–C₆-alkyl, C₁–C₆-alkoxy, hydroxyl or C₁–C₆-alkoxycarbonyl; R⁷ is C₁–C₆,-alkyl, C₃–C₆-alkenyl, C₃–C₆-haloalkenyl, C₃–C₆-alkynyl, C₃–C₆-haloalkynyl, C₃–C₆-cyloalkyl, C₁–C₂₀-alkylcarbonyl, C₂–C₆-alkenylcarbonyl, C₂–C₆-alkynylcarbonyl, C₃–C₆-cyloalkylcarbonyl, C₁–C₆-alkoxycarbonyl, C₃–C₆-alkenyloxycarbonyl, C₃–C₆-alkynyloxycarbonyl, (C₁–C₂₀-alkylthio)carbonyl, C₁–C₆-alkylaminocarbonyl, C₃–C₆-alkenylaminocarbonyl, C₃–C₆-alkynylaminocarbonyl, N,N-di-(C₁–C₆-alkyl)aminocarbonyl, N—(C₃–C₈-alkenyl)-N-(C₁–C₆-alkyl) aminocarbonyl, N—(C₃–C₆₋alkynyl)-N-(C₁–C₆-alkyl) aminocarbonyl, N—(C₁–C₆-alkoxy)-N-(C₁–C₆-alkyl) aminocarbonyl, N—(C₃–C₆-alkenyl)-N-(C₁–C₆-alkoxy) aminocarbonyl N—(C₃–C₆-alkynyl)-N-(C₁–C₆-alkoxy) aminocarbonyl, di-(C₁–C₆-alkyl)-aminothiocarbonyl, C₁–C₆-alkylcarbonyl-C₁–C₆-alkyl, C₁–C₆-alkoxyimino-C₁–C₆-alkyl, N—(C₁–C₆-alkylamino) imino-C₁–C₆-alkyl or N,N-di-(C₁–C₆-alkylamino)imino-C₁–C₆-alkyl, it being possible for the above-mentioned alkyl, cycloalkyl and alkoxy radicals to be partially or fully halogenated and/or to carry one to three of the following groups: cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio, di-(C₁–C₄-alkyl)amino, C₁–C₄-alkylcarbonyl, C₁–C₄-alkoxycarbonyl, C₁–C₄-alkoxy-C₁–C₄-alkoxycarbonyl, di-(C₁–C₄-alkyl)amino-C₁–C₄-alkoxycarbonyl, hydroxycarbonyl, C₁–C₄-alkylaminocarbonyl, di-(C₁–C₄-alkyl)aminocarbonyl, aminocarbonyl, C₁–C₄-alkylcarbonyloxy or C₃–C₈-cycloalkyl; phenyl, phenyl-C₁–C₆-alkyl, phenylcarbonyl-C₁–C₆-alkyl, phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl, phenoxy-C₁–C₆-alkylcarbonyl, phenylaminocarbonyl, N—(C₁–C₆-alkyl)-N-(phenyl)aminocarbonyl, or phenyl-C₂–C₆-alkenylcarbonyl, the phenyl radical of the 10 last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals; nitro, cyano, C₁–C₄-alkyl, C₁–C₁-halogenalkyl, C₁–C₄-alkoxy or C₁–C₄-haloalkoxy; R⁸,R⁹ are C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-haloalkenyl, C₃–C₆-alkynyl, C₃–C₆-haloalkynyl, C₃–C₆-cycloalkyl, hydroxyl, C₁–C₆-alkoxy, amino, C₁–C₆-alkylamino, C₁–C₆-haloalkylamino, di-(C₁–C₆-alkyl)amino or di-(C₁–C₆-haloalkyl)amino, the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three of the following groups: cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio, di-(C₁–C₄-alkyl)amino, C₁–C₄-alkylcarbonyl, C₁–C₄-alkoxycarbonyl, C₁–C₄-alkoxy-C₁–C₄-alkoxycarbonyl, di-(C₁–C₄-alkyl)amino-C₁–C₄-alkoxycarbonyl, hydroxycarbonyl, C₁–C₄-alkylaminocarbonyl, di-(C₁–C₄alkyl)aminocarbonyl, aminocarbonyl, C₁–C₄-alkylcarbonyloxy or C₃–C₆-cycloalkyl; phenyl, phenyl-C₁–C₆-alkyl phenoxy, the phenyl radical of the last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or C₁–C₄-haloalkoxy; R¹⁰ is C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-haloalkenyl, C₃–C₆-alkynyl, C₃–C₆-haloalkynyl, C₃–C₆-cycloalkyl, hydroxyl, C₁–C₆-alkoxy, C₃–C₆-alkenyloxy, C₃–C₆-alkynyloxy, amino, C₁–C₆-alkylamino, di-(C₁–C₆-alkyl)amino or C₁–C₆-alkylcarbonylamino, it being possible for the abovementioned alkyl, cycloalkyl and alkoxy radicals to be partially or fully halogenated and/or to carry one to three radicals from the following group: cyano, C₁–C₄-alkoxy, C₁–C₄-alkylthio, di-(C₁–C₄-alkyl)amino, C₁–C₄-alkylcarbonyl, C₁–C₄-alkoxycarbonyl, C₁–C₄-alkoxy-C₁–C₄-alkoxycarbonyl, di-(C₁–C₄-alkyl)aminoC₁–C₄alkoxycarbonyl, hydroxycarbonyl, C₁–C₄-alkylaminocarbonyl, di-(C₁–C₄-alkyl)aminocarbonyl, aminocarbonyl, C₁–C₄-alkylcarbonyloxy or C₃–C₆-cycloalkyl; phenyl or phenyl-C₁–C₆-alkyl, the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals: nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or C₁–C₄-haloalkoxy; R¹¹R¹² are C₁–C₆-alkyl, C₃–C₆-alkenyl, C₃–C₆-alkynyl or C₁–C₆-alkylcarbonyl; l is 0 to 6; m is 2 to 4; n is 1 to 5; p is 2 to 5; and their agriculturally useful salts.
 14. A cycycloyhexenonequinolinoyl compound of the formula I as claimed in claim 13, where R¹ is halogen, C₁–C₆-alkyl, C₁–C₆-haloalkyl, C₁–C₆-alkoxy, C₁–C₆-alkylthio, or phenylthio, it being possible for the last-mentioned radical to be partially or fully halogenated and/or to carry one to two of the substituents mentioned below: nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or C₁–C₄-haloalkoxy; R⁵ is halogen, OR⁷, SR⁷, SOR⁸, SO₂R⁸, OSO₂R⁸, OPR⁸R⁹, OPOR₈R⁹ OPSR⁸R⁹, NR¹⁰R¹¹ or N-bonded heterocyclyl.
 15. A cyclohexenonequinolinoyl compound of the formula I as claimed in claim 13, where R⁵ is halogen, OR⁷, NR¹⁰R¹¹ or N-bonded heterocyclyl.
 16. A cyclohexenonequinolinoyl compound of the formula I as claimed in claim 13, where R⁷ is C₁–C₆-alkyl, C₁–C₂₀-alkylcarbonyl, C₁–C₆-alkoxycarbonyl, (C₁–C₂₀-alkylthio)carbonyl, N,N-di-(C₁–C₆-alkyl)aminocarbonyl, phenyl, phenylcarbonyl or phenoxy-C₁–C₆-alkylcarbonyl, it being possible for the phenyl radical of the three last-mentioned substituents to be partially or fully halogenated and/or to carry one to three of the following radicals: nitro, cyano, C₁–C₄-alkyl, C₁–C₄-haloalkyl, C₁–C₄-alkoxy or C₁–C₄-haloalkoxy; R¹⁰ is C₁–C₆-alkyl or C₁–C₆-alkoxy; R¹¹ is C₁–C₆-alkyl.
 17. A process for preparing compounds of the formula I as claimed in claim 13 where R⁵=halogen, which comprises reacting a cyclohexanedione derivative of the formula III,

where the variables R¹ to R³ and I are each as defined in claim 13, with a halogenating agent.
 18. A process for preparing compounds of the formula I as claimed in claim 13 where R⁵=OR⁷, OSO₂R⁸, OPR⁸R⁹, OPOR₈R⁹ or OPSR⁸R⁹, which comprises reacting a cyclohexanedione derivative of the formula III,

where the variables R¹ to R³, and I are each as defined in claim 13, with a compound of the formula IVα, IVβ, IVγ, IVδ or IVε, L¹—R⁷  (IVα) L¹—SO₂R⁸  (IVβ) L¹—PR⁸R⁹  (IVγ) L¹—POR⁸R⁹  (IVγ) L¹—PSR⁸R⁹  (IVε) where the variables R⁷ to R⁹ are each as defined in claim 13 and L¹ is a nucleophilically replaceable leaving group.
 19. A process for preparing compounds of the formula I as claimed in claim 13 where R⁵=OR⁷, SR⁷, POR⁸R⁹, NR¹⁰R¹¹, ONR¹¹R¹², or N-linked heterocyclyl, which comprises reacting a compound of the formula I α(≡I where R⁵=halogen, OSO₂R⁸),

I where R⁵=halogen or OSO₂R⁸ where the variables R¹ to R³, and I are each as defined in claim 13, with a compound of the formula Vα, Vβ, Vγ, Vγ, Vδ, Vε, Vη, HOR⁷  (Vα) HSR⁷  (Vβ) HPOR⁸R⁹  (Vγ) HNR¹⁰R¹¹  (Vδ) HONR¹¹R¹²  (Vε) H(N-linked heterocyclyl) Vη where the variables R⁷ to R¹² are each as defined in claim 13, if appropriate in the presence of a base.
 20. A process for preparing compounds of the formula I as claimed in claim 13 where R⁵=SOR⁸, SO₂R⁸, which comprises reacting a compound of the formula Iβ (≡I where R⁵=SR⁸),

I where R⁵=SR⁶ where the variables R¹ to R⁵, R⁷, R⁸ and I are each as defined in claim 13, with an oxidizing agent.
 21. A composition, comprising a herbicidally effective amount of at least one cyclohexenonequinolinoyl compound of the formula I or an agriculturally useful salt of formula I as claimed in claim 13 and conventional crop protection formulation auxiliaries.
 22. A process for preparing a composition as claimed in claim 21, which comprises mixing a herbicidally effective amount of at least one cyclohexenonequinolinoyl derivative of the formula I or an agriculturally useful salt of formula I and conventional crop protection formulation auxiliaries.
 23. A method for controlling undesirable vegetation, which comprises allowing a herbicidally effective amount of at least one cyclohexenonequinolinoyl compound of the formula I or an agriculturally useful salt of formula I as claimed in claim 13 to act on plants, their habitat and/or on seeds. 